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Organic & Biomolecular Chemistry
Page 6 of 11
DOI: 10.1039/C7OB02691A
ARTICLE
Journal Name
Hz, 1H, pyridine 4-H), 7.40 (d, J = 8.2 Hz, 1H, indole 7-H), 7.24
(td, J = 7.6, 1.0 Hz, 1H, indole 6-H), 7.17 - 7.13 (m, 1H, indole 5-
H), 7.08 (d, J = 7.5 Hz, 1H, pyridine 5-H), 4.17 (q, J = 7.1 Hz, 2H,
-CH2CO2CH2CH3), 4.05 (s, 2H, -CH2CO2CH2CH3), 2.61 (s, 3H, -
CH3), 1.24 (t, J = 7.2 Hz, 3H, -CH2CO2CH2CH3); 13C NMR (125
MHz, CDCl3, ppm) δ 171.9, 158.4, 149.6, 137.2, 135.4, 134.2,
129.8, 123.4, 121.8, 119.9, 119.6, 118.7, 111.3, 106.8, 61.1,
31.7, 24.8, 14.4; HRMS (ESI) calcd for C18H18N2O2Li 301.1528,
found 301.1519.
Ethyl 2-(2-(pyridin-3-yl)-1H-indol-3-yl)acetate (4ab)
1
A yellow solid (80 mg, 0.29 mmol, 95%). H NMR (500 MHz,
CDCl3, ppm) δ 8.91 (d, J = 1.8 Hz, 1H, pyridine 2-H), 8.64 (dd, J =
4.8, 1.6 Hz, 1H, pyridine 6-H), 8.29 (br s, 1H, indole NH), 8.06
(dt, J = 7.9, 1.9 Hz, 1H, pyridine 4-H), 7.71 (d, J = 7.6 Hz, 1H,
indole 4-H), 7.45 - 7.40 (m, 2H, indole 7-H, pyridine 5-H), 7.28 -
7.24 (m, 1H, indole 6-H), 7.21 - 7.17 (m, 1H, indole 5-H), 4.18
(q,
J = 7.2 Hz, 2H, -CH2CO2CH2CH3), 3.81 (s, 2H, -
CH2CO2CH2CH3), 1.29 – 1.24 (m, 3H, -CH2CO2CH2CH3); 13C NMR
Ethyl 2-(2-(5-methylpyridin-2-yl)-1H-indol-3-yl)acetate (4ag)
1
132.8, 129.0, 128.7, 123.9, 123.3, 120.5, 119.7, 111.2, 107.5, A yellow solid (79 mg, 0.27 mmol, 89%). H NMR (500 MHz,
(125 MHz, CDCl3, ppm) δ 172.0, 149.2, 149.1, 136.3, 135.8,
61.2, 31.2, 14.4; HRMS (ESI) calcd for C17H16N2O2 348.1688, CDCl3, ppm) δ 9.52 (d, J = 13.7 Hz, 1H, indole NH), 8.47 (s, 1H,
found 348.1683.
pyridine 6-H), 7.91 (d, J = 8.1 Hz, 1H, pyridine 3-H), 7.71 (d, J =
7.9 Hz, 1H, indole 4-H), 7.60 (dd, J = 8.1, 1.7 Hz, 1H, pyridine 4-
H), 7.38 (dd, J = 8.1, 0.8 Hz, 1H, indole 7-H), 7.25 - 7.21 (m, 1H,
indole 6-H), 7.17 - 7.12 (m, 1H, indole 5-H), 4.17 (q, J = 7.1 Hz,
2H, -CH2CO2CH2CH3), 4.03 (s, 2H, -CH2CO2CH2CH3), 2.38 (s, 3H, -
CH3), 1.24 (t, J = 7.1 Hz, 3H, -CH2CO2CH2CH3); 13C NMR (125
MHz, CDCl3, ppm) δ 171.9, 150.0, 147.8, 137.5, 135.4, 134.2,
131.9, 129.8, 123.4, 121.2, 119.9, 119.5, 111.3, 106.4, 61.1,
31.7, 18.4, 14.4; HRMS (ESI) calcd for C18H18N2O2Na 317.1266,
found 317.1261.
Ethyl 2-(2-(pyridin-4-yl)-1H-indol-3-yl)acetate (4ac)
A yellow solid (80 mg, 0.29 mmol, 95%). Spectroscopic data
were in good agreement with the literature.7 1H NMR (500
MHz, CDCl3, ppm) δ 8.70 (d, J = 6.0 Hz, 2H, pyridine 2-H, 6-H),
8.53 (br s, 1H, indole NH), 7.72 (d, J = 8.1 Hz, 1H, indole 4-H),
7.63 - 7.60 (m, 2H, pyridine 3-H, 5-H), 7.40 (d, J = 8.1 Hz, 1H,
indole 7-H), 7.30 - 7.26 (m, 1H, indole 6-H), 7.21 - 7.17 (m, 1H,
indole 5-H), 4.20 (q, J = 7.2 Hz, 2H, -CH2CO2CH2CH3), 3.88 (s,
2H, -CH2CO2CH2CH3), 1.27 (t, J = 7.1 Hz, 3H, -CH2CO2CH2CH3).
Ethyl 2-(2-(4-methylpyridin-2-yl)-1H-indol-3-yl)acetate (4ah)
1
A yellow solid (80 mg, 0.27 mmol, 91%). H NMR (500 MHz,
Ethyl 2-(2-(6-bromopyridin-2-yl)-1H-indol-3-yl)acetate (4ad)
1
A white solid (96 mg, 0.27 mmol, 89%). H NMR (500 MHz,
CDCl3, ppm) δ 9.92 (br s, 1H, indole NH), 8.50 (d, J = 4.9 Hz, 1H,
pyridine 6-H), 7.88 - 7.84 (m, 1H, pyridine 3-H), 7.73 (d, J = 7.9
Hz, 1H, indole 4-H), 7.35 (dd, J = 8.1, 0.8 Hz, 1H, indole 7-H),
7.22 (ddd, J = 8.0, 7.1, 0.9 Hz, 1H, indole 6-H), 7.17 - 7.13 (m,
1H, indole 5-H), 7.06 - 7.03 (m, 1H, pyridine 5-H), 4.20 (q, J =
7.1 Hz, 2H, -CH2CO2CH2CH3), 4.07 (s, 2H, -CH2CO2CH2CH3), 2.45
(s, 3H, -CH3), 1.27 (t, J = 7.1 Hz, 3H, -CH2CO2CH2CH3); 13C NMR
(125 MHz, CDCl3, ppm) δ 171.9, 150.3, 149.3, 148.1, 135.6,
134.2, 129.7, 123.4, 123.3, 122.7, 119.9, 119.6, 111.4, 106.8,
61.1, 31.8, 21.5, 14.4; HRMS (ESI) calcd for C18H18N2O2Li
301.1528, found 301.1524.
DMSO-d6, ppm) δ 11.65 (s, 1H, indole NH), 7.92 (d, J = 7.6 Hz,
1H, pyridine 3-H), 7.86 (t, J = 7.8 Hz, 1H, pyridine 4-H), 7.62 (d,
J = 7.9 Hz, 1H, indole 4-H), 7.52 (d, J = 7.6 Hz, 1H, pyridine 5-H),
7.45 (d, J = 8.1 Hz, 1H, indole 7-H), 7.20 (t, J = 7.2 Hz, 1H, indole
6-H), 7.09 - 7.02 (m, 1H, indole 5-H), 4.16 (s, 2H, -
CH2CO2CH2CH3), 4.07 (q, J = 7.2 Hz, 2H, -CH2CO2CH2CH3), 1.17
(t, J = 7.1 Hz, 3H, -CH2CO2CH2CH3); 13C NMR (125 MHz, DMSO-
d6, ppm) δ 171.3, 152.2, 140.8, 140.2, 136.2, 131.6, 128.9,
125.6, 123.3, 119.4, 119.4, 119.2, 111.7, 109.4, 60.0, 30.5,
14.1; HRMS (ESI) calcd for C17H15BrN2ONa 381.0215, found
381.0215.
Ethyl 2-(2-(3-methylpyridin-2-yl)-1H-indol-3-yl)acetate (4ai)
1
A yellow solid (82 mg, 0.28 mmol, 94%). H NMR (500 MHz,
Ethyl 2-(2-(6-methoxypyridin-2-yl)-1H-indol-3-yl)acetate (4ae)
1
A white solid (87 mg, 0.28 mmol, 94%). H NMR (500 MHz,
CDCl3, ppm) δ 8.95 (br s, 1H, indole NH), 8.38 (d, J = 4.1 Hz, 1H,
pyridine 6-H), 7.64 (d, J = 7.8 Hz, 1H, indole 4-H or pyridine 4-
H), 7.61 (dd, J = 7.8, 0.8 Hz, 1H, indole 4-H or pyridine 4-H),
7.32 (d, J = 8.1 Hz, 1H, indole 7-H), 7.21 - 7.12 (m, 3H, indole 5-
H, 6-H, pyridine 5-H), 4.06 (q, J = 7.1 Hz, 2H, -CH2CO2CH2CH3),
3.75 (s, 2H, -CH2CO2CH2CH3), 2.35 (s, 3H, -CH3), 1.16 (t, J = 7.1
Hz, 3H, -CH2CO2CH2CH3); 13C NMR (125 MHz, CDCl3, ppm) δ
171.9, 150.6, 146.6, 139.0, 136.1, 133.8, 133.3, 128.2, 123.0,
122.7, 119.8, 119.4, 111.4, 107.9, 60.7, 31.2, 19.1, 14.2; HRMS
(ESI) calcd for C18H18N2O2Li 301.1528, found 301.1523.
CDCl3, ppm) δ 9.18 (br s, 1H, indole NH), 7.70 (d, J = 7.9 Hz, 1H,
indole 4-H), 7.67 (dd, J = 8.2, 7.6 Hz, 1H, pyridine 4-H), 7.51 (d,
J = 7.5 Hz, 1H, pyridine 3-H), 7.42 (d, J = 8.2 Hz, 1H, indole 7-H),
7.27 - 7.23 (m, 1H, indole 6-H), 7.18 - 7.14 (m, 1H, indole 5-H),
6.71 - 6.67 (m, 1H, pyridine 5-H), 4.16 (q, J = 7.2 Hz, 2H, -
CH2CO2CH2CH3), 4.09 (s, 2H, -CH2CO2CH2CH3), 4.05 (s, 3H, -
OCH3), 1.23 (t, J = 7.1 Hz, 3H, -CH2CO2CH2CH3); 13C NMR (125
MHz, CDCl3, ppm) δ 171.9, 163.8, 147.9, 139.5, 135.3, 133.9,
129.8, 123.5, 120.1, 119.6, 114.3, 111.2, 109.6, 107.3, 61.1,
53.6, 31.7, 14.4; HRMS (ESI) calcd for C18H18N2O3Li 317.1477,
found 317.1477.
Ethyl 2-(2-(quinolin-2-yl)-1H-indol-3-yl)acetate (4aj)
1
A brown solid (85 mg, 0.26 mmol, 86%). H NMR (500 MHz,
Ethyl 2-(2-(6-methylpyridin-2-yl)-1H-indol-3-yl)acetate (4af)
1
A yellow solid (74 mg, 0.25 mmol, 84%). H NMR (500 MHz,
CDCl3, ppm) δ 9.72 (br s, 1H, indole NH), 8.23 (d, J = 8.5 Hz, 1H,
quinoline 4-H), 8.14 (d, J = 8.7 Hz, 1H, quinoline 3-H), 8.10 (d, J
= 8.4 Hz, 1H, quinoline 8-H), 7.84 - 7.81 (m, 1H, quinoline 5-H),
7.77 - 7.71 (m, 2H, indole 4-H, quinoline 7-H), 7.53 (ddd, J =
CDCl3, ppm) δ 9.49 (br s, 1H, indole NH), 7.80 (d, J = 7.8 Hz, 1H,
indole 4-H), 7.71 (d, J = 7.8 Hz, 1H, pyridine 3-H), 7.67 (t, J = 7.7
6 | J. Name., 2012, 00, 1-3
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