The Journal of Organic Chemistry
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Hexane:EtOAc = 30:70, Rf = 0.5) to afford pure 7b (102 mg, 68%) as
off-white solid. 1H NMR (600 MHz, DMSO-d6) δ 8.34 (bs, 1H), 8.33
(s, 1H), 7.90−7.80 (m, 1H), 7.44−7.28 (m, 3H), 6.84−6.77 (m, 2H),
6.71−6.63 (m, 2H), 4.33 (d, J = 5.0 Hz, 1H), 3.69 (d, J = 10.0 Hz,
1H), 3.64 (d, J = 1.8 Hz, 3H), 3.28 (dd, J = 10.1, 1.3 Hz, 1H). 13C
NMR {1H} (150 MHz, DMSO- d6) δ 174.9, 155.0, 137.9, 130.2,
128.6, 126.5, 126.1, 122.9, 120.4, 113.3, 64.8, 54.9, 53.3, 43.8. HRMS
(ESI+) m/z [M + Na]+ calcd. for [C18H16N2O2+Na]: 315.1104,
found 315.1103. IR (neat) νmax 3247, 3158, 2918, 2866, 1701, 1510,
1502, 1475, 1179, 1028, 979, 935, 808, 742, 561 cm−1.
Compound 7c. The desired compound 7c was synthesized from 3
and 2c (226 mg, 0.8 mmol) by following the standard procedure. The
crude product was purified by column chromatography (SiO2,
Hexane:EtOAc = 30:70, Rf = 0.5) to afford pure 7c (113 mg, 57%)
as white solid. 1H NMR (600 MHz, DMSO-d6) δ 8.43 (bs, 1H), 8.40
(s, 1H), 7.89−7.83 (m, 1H), 7.41 (dd, J = 6.9, 1.8 Hz, 1H), 7.39−
7.33 (m, 2H), 7.12 (d, J = 2.1 Hz, 1H), 6.84 (d, J = 8.6 Hz, 1H), 6.80
(dd, J = 8.5, 2.1 Hz, 1H), 4.40 (s, 1H), 3.73 (s, 3H), 3.71 (d, J = 10.0
Hz, 1H), 3.33−3.25 (m, 1H). 13C NMR {1H} (150 MHz, DMSO-d6)
δ 174.8, 174.4, 155.0, 154.4, 137.8, 133.2, 129.7, 128.8, 127.8, 126.7,
123.0, 120.5, 112.0, 109.8, 64.8, 56.1, 52.6, 43.8. HRMS (ESI+) m/z
[M + H]+ calcd. for [C18H16BrN2O2]: 371.0389, found 371.0391. IR
(neat) νmax 3188, 2829, 2833, 1701, 1599, 1494, 1159, 1054, 1017,
879, 742, 533, 479, 432 cm−1.
Compound 7d. The desired compound 7d was synthesized from 3
and 2d (179 mg, 0.8 mmol) by following the standard procedure. The
crude product was purified by column chromatography (SiO2,
Hexane:EtOAc = 30:70, Rf = 0.5) to afford pure 7d (116 mg, 70%)
as Off-white solid. 1H NMR (600 MHz, TFA-d) δ 8.40 (s, 1H), 8.39
(bs, 1H), 7.91−7.82 (m, 1H), 7.43−7.39 (m, 1H), 7.39−7.32 (m,
2H), 6.87 (t, J = 8.7 Hz, 1H), 6.79 (dd, J = 12.7, 2.1 Hz, 1H), 6.60−
6.55 (m, 1H), 4.39 (s, 1H), 3.72 (s, 3H), 3.70 (d, J = 10.1 Hz, 1H),
3.28 (dd, J = 10.1, 1.3 Hz, 1H). 13C NMR {1H} (150 MHz, DMSO-
d6) δ 174.8, 174.4, 151.4, 150.6, 149.8, 146.1, 137.9, 128.7, 126.9,
126.6, 125.4, 123.0, 120.5, 116.4, 113.1, 64.8, 55.8, 52.9, 43.8. HRMS
(ESI+) m/z [M + H]+ calcd. for [C18H16FN2O2]: 311.1190, found
311.1190. IR (neat) νmax 3231, 3106, 2929, 2651, 1698, 1515, 1477,
1214, 1126, 1023, 929, 868, 747, 544, 473 cm−1.
(s, 1H), 7.87−7.85 (m, 1H), 7.39−7.34 (m, 3H), 6.93−6.91 (d, J = 8
Hz, 2H), 6.78−6.76 (d, J = 8 Hz, 2H), 4.33 (s, 1H), 3.71−3.68 (d, J =
8 Hz, 1H), 3.30−3.27 (d, J = 12 Hz, 1H), 2.17 (s, 3H). 13C NMR
{1H} (100 MHz, DMSO-d6) δ 174.7, 174.5, 155.1, 138.2, 136.0,
131.2, 128.8, 128.4, 128.3, 126.3, 122.7, 120.4, 64.6, 53.5, 43.8, 20.5.
HRMS (ESI+) m/z [M + H]+ Calcd for C18H17N2O: 277.1335, found
277.1323. IR (neat) νmax 3144, 3022, 2957, 2840, 1696, 1537, 1476,
1428, 1073, 1016, 735, 672, 563, 542, 511 cm−1.
Compound 7h. The desired compound 7h was synthesized from 3
and 2h (145 mg, 0.8 mmol) by following the standard procedure. The
crude product was purified by column chromatography (SiO2,
Hexane:EtOAc = 30:70, Rf = 0.5) to afford pure 7h (90 mg, 63%)
as yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 7.83 (s, 1H), 7.49
(d, J = 8 Hz, 1H), 7.30 (d, J = 4 Hz, 1H), 6.97 (t, J = 16 Hz, 1H),
6.88 (d, J = 4 Hz, 1H), 6.62 (t, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H),
6.36 (bs, 1H), 5.12 (s, 1H), 3.76 (s, 1H), 3.66 (d, J = 8 Hz, 1H), 3.48
(d, J = 12 Hz, 1H). 13C NMR {1H} (100 MHz, DMSO-d6) δ 173.7,
150.4, 144.7, 143.2, 130.9, 130.8, 128.6, 123.9, 122.0, 117.6, 109.0,
70.1, 66.8, 55.9, 52.6. HRMS (ESI+) m/z [M + H]+ Calcd for
C15H12N2OS: 269.0743, found 269.0756. IR (neat) νmax 3328, 3152,
3068, 2943, 2816, 1702, 1522, 1470, 1432, 1256, 782, 716, 657, 602,
595 cm−1.
Compound 7i. The desired compound 7i was synthesized from 3
and 2i (164 mg, 0.8 mmol) by following the standard procedure. The
crude product was purified by column chromatography (SiO2,
Hexane:EtOAc = 30:70, Rf = 0.5) to afford pure 7i (102 mg, 66%)
as white solid. 1H NMR (400 MHz, CDCl3) δ 7.98 (s, 1H), 7.58 (d, J
= 8 Hz, 2H), 7.43−7.35 (m, 2H), 7.23−7.17 (m, 3H), 6.91 (d, J = 12
Hz, 2H), 4.08 (s, 1H), 3.64 (s, 2H) 1.23 (s, 9H). 13C NMR {1H}
(100 MHz, CDCl3) δ 176.9, 173.1, 155.1, 150.8, 139.3, 130.2, 129.2,
128.0, 127.2, 125.8, 121.7, 121.4, 64.2, 54.2, 45.2, 34.6, 31.3. HRMS
(ESI+) m/z [M + H]+ Calcd for C21H22N2O: 319.1805, found
319.1822. IR (neat) νmax 3190, 2955, 2888, 2832, 2675, 1705, 1661,
1478, 1170, 1097, 776, 655, 591, 453, 416 cm−1.
Compound 7j. The desired compound 7j was synthesized from 3
and 2j (155 mg, 0.8 mmol) by following the standard procedure. The
crude product was purified by column chromatography (SiO2,
Hexane:EtOAc = 30:70, Rf = 0.5) to afford pure 7j (105 mg, 71%)
as yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.41 (s, 1H), 8.35
(s, 1H), 7.89−7.87 (m, 1H), 7.37−7.35 (m, 3H), 6.97−6.89 (m, 4H),
4.44 (s, 1H), 3.72 (d, J = 8 Hz, 1H), 3.28 (d, J = 12 Hz, 1H). 13C
NMR {1H} (100 MHz, DMSO-d6) δ 174.8, 174.3, 155.0, 151.4,
149.8, 146.1, 146.0, 137.8, 128.6, 126.9, 126.5, 125.4, 125.4, 122.9,
120.4, 116.4, 116.3, 113.0, 64.7, 55.7, 52.8, 43.5. HRMS (ESI+) m/z
[M + H]+ Calcd for C17H14FN2O: 281.1085, found 281.1091. IR
(neat) νmax 3157, 3080, 2926, 2892, 1700, 1512, 1490, 1116, 1053,
730, 673, 570, 550, 462, 437 cm−1.
Compound 7e. The desired compound 7e was synthesized from 3
and 2e (168 mg, 0.8 mmol) by following the standard procedure. The
crude product was purified by column chromatography (SiO2,
Hexane:EtOAc = 30:70, Rf = 0.5) to afford pure 7e (107 mg, 63%)
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as white solid. H NMR (400 MHz, DMSO-d6) δ 8.45 (s, 1H), 8.35
(s, 1H), 7.89−7.87 (m, 1H), 7.42−7.38 (m, 1H), 7.36 (t, J = 4 Hz,
2H), 7.18 (d, J = 12 Hz, 2H), 6.90 (d, J = 8 Hz, 2H), 4.46 (s, 1H),
3.73 (d, J = 8 Hz, 1H), 3.29 (d, J = 8 Hz, 1H). 13C NMR {1H} (100
MHz, DMSO-d6) δ 174.4, 174.2, 155.1, 137.7, 133.2, 131.8, 130.9,
128.7, 127.9, 126.6, 122.9, 120.5, 64.6, 53.1, 43.9. HRMS (ESI+) m/z
[M + H]+ Calcd for C17H14ClN2O: 297.0789, found 297.0793. IR
(neat) νmax 3186, 3094, 2963, 2876, 1694, 1555, 1493, 1091, 1016,
759, 680, 576, 500, 465, 432 cm−1.
Compound 7k. The desired compound 7k was synthesized from 3
and 2k (204 mg, 0.8 mmol) by following the standard procedure. The
crude product was purified by column chromatography (SiO2,
Hexane:EtOAc = 30:70, Rf = 0.5) to afford pure 7k (104 mg, 58%)
as white solid. 1H NMR (400 MHz, CDCl3) δ 7.98 (s, 1H), 7.57 (d, J
= 8 Hz, 1H), 7.46−7.38 (m, 2H), 7.34 (d, J = 8 Hz, 1H), 7.14 (s,
2H), 7.0 (t, J = 8 Hz, 1H), 6.84 (d, J = 8 Hz, 1H), 6.41 (s, 1H), 4.08
(s, 1H), 3.72 (d, J = 12 Hz, 1H), 3.59 (d, J = 12 Hz, 1H). 13C NMR
{1H} (100 MHz, CDCl3) δ 174.9, 174.2, 171.7, 155.6, 154.9, 140.7,
137.8, 135.0, 129.3, 128.9, 128.8, 127.7, 126.8, 124.5, 122.2, 121.7,
60.5, 53.1, 51.5, 40.5, 40.2. HRMS (ESI+) m/z [M + H]+ Calcd for
C17H14BrN2O: 341.0284, found 341.0281. IR (neat) νmax 3192, 3090,
2870, 2854, 1700, 1580, 1453, 1072, 1020, 756, 663, 575, 567, 490,
431 cm−1.
Compound 7f. The desired compounds 7f was synthesized from 3
and 2f (140 mg, 0.8 mmol) by following the standard procedure. The
crude product was purified by column chromatography (SiO2,
Hexane: EtOAc = 30:70, Rf = 0.5) to afford pure 7f (100 mg,
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74%) as yellow solid. H NMR (600 MHz, TFA-d) δ 9.7 (s, 1H),
8.44−8.42 (d, J = 16 Hz, 1H), 8.25−8.21 (m, 1H), 8.11−8.07 (m,
2H), 7.72−7.70 (m, 1H), 7.69−7.60 (m, 2H), 7.32−7.30 (m, 2H),
5.32 (s, 1H), 4.68−4.65 (d, J = 18 Hz, 1H), 4.55−4.52 (d, J = 18 Hz,
1H). 13C NMR {1H} (150 MHz, DMSO-d6) δ 174.7, 174.7, 156.6,
155.0, 138.2, 134.3, 129.1, 128.6, 127.9, 127.1, 126.6, 122.9, 120.4,
64.7, 54.0, 44.0. HRMS (ESI+) m/z [M + Na]+ calcd. for
[C17H14N2O+Na]: 285.0998, found 285.0998. IR (neat) νmax 3225,
3166, 2920, 1699, 1600, 1475, 1253, 1158, 1051, 976, 927, 698, 544,
437, 428 cm−1.
Compound 7l. The desired compound 7l was synthesized from 3
and 2l (155 mg, 0.8 mmol) by following the standard procedure. The
crude product was purified by column chromatography (SiO2,
Hexane:EtOAc = 30:70, Rf = 0.5) to afford pure 7l (91 mg, 62%)
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Compound 7g. The desired compound 7g was synthesized from 3
and 2g (152 mg, 0.8 mmol) by following the standard procedure. The
crude product was purified by column chromatography (SiO2,
Hexane:EtOAc = 30:70, Rf = 0.5) to afford pure 7g (114 mg, 77%)
as white solid. H NMR (400 MHz, DMSO-d6) δ 8.44 (s, 1H), 8.39
(s, 1H), 7.89−7.87 (m, 1H), 7.42−7.40 (m, 1H), 7.39−7.35 (m, 2H),
7.17−7.12 (m, 1H), 6.97 (t, J = 12 Hz, 1H), 6.77 (d, J = 12 Hz, 1H),
6.65 (d, J = 8 Hz, 1H), 4.48 (s, 1H), 3.73 (d, J = 8 Hz, 1H), 3.30 (d, J
= 12 Hz, 1H). 13C NMR {1H} (100 MHz, DMSO-d6) δ 174.7, 174.7,
1
as white solid. H NMR (400 MHz, DMSO-d6) δ 8.36 (s, 1H), 8.30
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J. Org. Chem. 2021, 86, 5234−5244