Molecules 2021, 26, 2801
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(101 MHz, CDCl3)
δ
166.9, 161.2, 140.5, 134.9, 133.0, 130.5, 129.5, 128.8, 121.1, 117.5, 114.9,
92.0, 80.3, 55.6, 53.2, 49.7. HRMS ESI [M + Na]+ calcd for C20H16ClN3O3Na+ 404.0772,
found 404.0771.
Methyl 2-{4-[(4-chlorophenyl)ethynyl]-5-(4-phenoxyphenyl)-1H-1,2,3-triazol-1-yl}acetate (10b).
This compound was synthesized according to the general procedure from 5-iodo-1H-1,2,3-
triazole 8a (150 mg, 0.374 mmol) and boronic acid 9b (160 mg, 0.748 mmol). Reaction time—4 h.
The crude product was purified by column chromatography (eluent: hexane/EtOAc = 2:1) to
afford a colorless oil (102 mg, 61% yield); 1H NMR (400 MHz, CDCl3)
δ
7.50–7.45 (m, 2HAr),
7.44–7.37 (m, 4HAr), 7.32–7.27 (m, 2HAr), 7.24–7.18 (m, 1HAr), 7.14–7.07 (m, 4HAr), 5.12 (s, 2H,
CH2), 3.79 (s, 3H, CH3). 13C NMR (101 MHz, DMSO)
166.9, 159.7, 155.8, 140.1, 135.0, 133.0,
δ
130.7, 130.2, 129.6, 128.9, 124.7, 121.0, 120.2, 119.5, 118.5, 92.2, 80.2, 53.3, 49.7. HRMS ESI [M +
Na]+ calcd for C25H18ClN3O3Na+ 466.0929, found 466.0926.
Methyl 2-{4-[(4-chlorophenyl)ethynyl]-5-[4-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-1-yl}acetate
(10c). This compound was synthesized according to the general procedure from 5-iodo-1H-
1,2,3-triazole 8a (80 mg, 0.199 mmol) and boronic acid 9c (75 mg, 0.398 mmol). Reaction time—
7 h. The crude product was purified by column chromatography (eluent: hexane/acetone = 5:1)
to afford a yellow oil (35 mg, 42% yield); 1H NMR (400 MHz, CDCl3)
δ
7.82 (d, J = 8.2 Hz,
2HAr), 7.68 (d, J = 8.2 Hz, 2HAr), 7.42–7.35 (m, 2HAr), 7.34–7.28 (m, 2HAr), 5.14 (s, 2H, CH2),
3.79 (s, 3H, CH3). 13C NMR (101 MHz, CDCl3)
166.6 (C), 140.0 (C), 135.3 (C), 133.0 (2CH),
δ
132.45 (q, 2JC-F = 33.0 Hz, C), 130.3 (C), 129.6 (2CH), 129.4 (C), 129.0 (2CH), 126.43 (q, 3JC-F = 3.7
Hz, 2CH), 123.73 (q, 1JC-F = 272.6 Hz, C), 120.6 (C), 92.7 (C), 79.4 (C), 53.4 (CH3), 49.8 (CH2).
HRMS ESI [M + Na]+ calcd for C20H13ClF3N3O2Na+ 442.0541, found 442.0539. Appropriate
crystals for X-Ray analysis were obtained from acetonitrile solution. Crystallographic data for
10c were deposited with the Cambridge Crystallographic Data Centre, no. CCDC 2077046.
Methyl 2-{4-[(4-cyanophenyl)ethynyl]-5-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl}acetate (10d).
This compound was synthesized according to the general procedure from 5-iodo-1H-1,2,3-
triazole 8b (90 mg, 0.230 mmol) and boronic acid 9a (70 mg, 0.460 mmol). Reaction time—7 h.
The crude product was purified by column chromatography (eluent: hexane/acetone = 5:1)
to afford a colorless crystals (59 mg, 69% yield): mp 146
MHz, CDCl3) 7.63–7.58 (m, 2HAr), 7.56–7.51 (m, 2HAr), 7.46–7.41 (m, 2HAr), 7.09–7.03 (m, 2H,
CHAr), 5.12 (s, 2H, CH2), 3.89 (s, 3H, CH3), 3.79 (s, 3H, CH3). 13C NMR (101 MHz, CDCl3)
−
147 ◦C (acetonitrile); 1H NMR (400
δ
δ
166.8, 161.4, 141.1, 132.2, 132.2, 130.5, 128.9, 127.5, 118.5, 117.3, 115.0, 112.1, 91.5, 83.8, 55.6, 53.3,
49.7. HRMS ESI [M + Na]+ calcd for C21H16N4O3Na+ 395.1115, found 395.1110.
Methyl 2-{4-[(4-cyanophenyl)ethynyl]-5-(naphthalen-2-yl)-1H-1,2,3-triazol-1-yl}acetate (10e).
This compound was synthesized according to the general procedure from 5-iodo-1H-1,2,3-
triazole 8b (75 mg, 0.191 mmol) and boronic acid 9d (66 mg, 0.383 mmol). Reaction
time—5 h. The crude product was purified by column chromatography (eluent: hex-
◦
ane/EtOAc = 2:1) to afford a white solid (43 mg, 75% yield): mp 129
MHz, CDCl3)
(m, 2HAr), 5.20 (s, 2H, CH2), 3.78 (s, 3H, CH3). 13C NMR (101 MHz, CDCl3)
−
131 C; 1H NMR (400
δ
8.05–8.00 (m, 2HAr), 7.96–7.90 (m, 2HAr), 7.66–7.55 (m, 5HAr), 7.53–7.47
166.8, 141.3,
δ
133.9, 133.2, 132.2, 132.2, 129.5, 129.5, 129.3, 128.5, 128.2, 128.1, 127.5, 127.4, 125.5, 122.6,
118.5, 112.1, 91.7, 83.6, 53.3, 49.8. HRMS ESI [M + Na]+ calcd for C24H16N4O2Na+ 415.1165,
found 415.1163.
Methyl 2-(5-{4-[(tert-butoxycarbonyl)amino]phenyl}-4-[(4-cyanophenyl)ethynyl]-1H-1,2,3-
triazol-1-yl)acetate (10f). This compound was synthesized according to the general procedure
from 5-iodo-1H-1,2,3-triazole 8b (80 mg, 0.204 mmol) and boronic acid 9e (97 mg, 0.408
mmol). Reaction time—5 h. The crude product was purified by column chromatography
◦
(eluent: hexane/EtOAc = 2:1) to afford a white solid (53 mg, 57% yield): mp 87
NMR (400 MHz, CDCl3)
5.12 (s, 2H, CH2), 3.78 (s, 3H, CH3), 1.54 (s, 9H, CH3). 13C NMR (101 MHz, CDCl3)
−
88 C; 1H
δ
7.63–7.50 (m, 6HAr), 7.44 (d, J = 8.6 Hz, 2H), 6.68 (s, 1H, NH),
166.8,
δ
152.5, 140.9, 140.7, 132.2, 132.2, 129. 9, 129.0, 127.5, 119.2, 118.9, 118.5, 112.1, 91.5, 83.7, 81. 6,
53.3, 49.7, 28.4. HRMS ESI [M + Na]+ calcd for C25H23N5O4Na+ 480.1642, found 480.1642.
Methyl 2-[5-(4-cyanophenyl)-4-{[4-(dimethylamino)phenyl]ethynyl}-1H-1,2,3-triazol-1-yl]acetate
(10g). This compound was synthesized according to the general procedure from 5-iodo-1H-1,2,3-