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5.1.33. 2-[1-(4-Nitrobenzyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-4-
5.1.40. 2-[1-(1,10-Biphenyl-4-ylmethyl)-1H-indol-3-yl]-2-oxo-
yl)acetamide (42)
N-(pyridin-4-yl)acetamide (49)
It was synthesized via route B from 17 using 4-nitrobenzyl chlo-
ride. Yield 54%, mp >250 °C. 1H NMR (250 MHz, DMSO-d6): d 5.82
(s, 2H), 7.30–7.36 (m, 2H), 7.53 (d, J = 8.6 Hz, 2H), 7.58 (d,
J = 8.0 Hz, 2H), 7.86 (d, J = 5.9 Hz, 2H), 8.21 (d, J = 8.6 Hz, 2H),
8.32 (d, J = 7.6 Hz, 1H), 8.52 (d, J = 5.9 Hz, 2H), 9.08 (s, 1H), 11.11
(s, 1H). ESMS m/z 401.4 (MH+). Anal. (C22H16N4O4) C, H, N.
It was synthesized via route B from 17 using 4-(chloromethyl)-
1,10-biphenyl. Yield 96%, mp 235–237 °C. 1H NMR (250 MHz,
DMSO-d6): d 5.71 (s, 2H), 7.35–7.39 (m, 3H), 7.43–7.50 (m, 4H),
7.63–7.74 (m, 5H), 7.92 (d, J = 6.2 Hz, 2H), 8.34–8.38 (m, 1H),
8.57 (d, J = 6.2 Hz, 2H), 9.10 (s, 1H), 11.18 (s, 1H). ESMS m/z
432.5 (MH+). Anal. (C28H21N3O2) C, H, N.
5.1.34. 2-[1-(4-(Trifluoromethyl)benzyl)-1H-indol-3-yl]-2-oxo-
N-(pyridin-4-yl)acetamide (43)
5.1.41. 2–Oxo-N-(pyridin-4-yl)-2-[1-(pyridin-4-ylmethyl)-1H-
indol-3-yl]acetamide (50)
It was synthesized via route B from 17 using 4-(trifluoro-
methyl)benzyl chloride. Yield 53%, mp >250 °C. 1H NMR
(250 MHz, DMSO-d6): d 5.76 (s, 2H), 7.30–7.36 (m, 2H), 7.50 (d,
J = 8.1 Hz, 2H), 7.60 (d, J = 7.9 Hz, 1H), 7.72 (d, J = 8.2 Hz, 2H),
7.86 (d, J = 6.0 Hz, 2H), 8.32 (d, J = 7.5 Hz, 1H), 8.52 (d, J = 6.0 Hz,
2H), 9.06 (s, 1H), 11.10 (s, 1H). ESMS m/z 424.4 (MH+). Anal.
(C23H16F3N3O2) C, H, N.
It was synthesized via route B from 17 using 4-picolyl chloride
hydrochloride. Yield 50%, mp 232–234 °C. 1H NMR (250 MHz,
DMSO-d6): d 5.75 (s, 2H), 7.25 (d, J = 6.3 Hz, 2H), 7.33–7.41 (m,
2H), 7.57 (dd, J = 6.8, 1.2 Hz, 1H), 7.90 (d, J = 6.4 Hz, 2H), 8.35 (m,
1H), 8.55–8.57 (m, 4H), 9.08 (s, 1H), 11.16 (s, 1H). ESMS m/z
357.2 (MH+). Anal. (C21H16N4O2) C, H, N.
5.1.42. 2-Oxo-N-(pyridin-4-yl)-2-[1-(pyridin-3-ylmethyl)-1H-
indol-3-yl]acetamide (51)
5.1.35. 2-[1-(4-Methoxybenzyl)-1H-indol-3-yl]-2-oxo-N-
(pyridin-4-yl)acetamide (44)
It was synthesized via route B from 17 using 3-chloromethyl-
pyridine. Yield 22%, mp 178–180 °C. 1H NMR (250 MHz, DMSO-
d6): d 5.71 (s, 2H), 7.35–7.42 (m, 3H), 7.73–7.76 (m, 2H), 7.89 (d,
J = 5.1 Hz, 2H), 8.33 (m, 1H), 8.52–8.56 (m, 3H), 8.70 (s, 1H), 9.08
(s, 1H), 11.14 (s, 1H). ESMS m/z 357.4 (MH+). Anal. (C21H16N4O2)
C, H, N.
It was synthesized via route B from 17 using 4-methoxybenzyl
chloride. Yield 75%, mp 173–174 °C. 1H NMR (250 MHz, DMSO-d6):
d 3.71 (s, 3H), 5.53 (s, 2H), 6.91 (d, J = 8.6 Hz, 2H), 7.30–7.33 (m,
4H), 7.66–7.68 (m, 1H), 7.86 (d, J = 6.0 Hz, 2H), 8.28–8.30 (m,
1H), 8.52 (d, J = 6.0 Hz, 2H), 8.96 (s, 1H), 11.07 (s, 1H). ESMS m/z
386.4 (MH+). Anal. (C23H19N3O3) C, H, N.
5.1.43. 2–Oxo-N-(pyridin-4-yl)-2-[1-(pyridin-2-ylmethyl)-1H-
indol-3-yl]acetamide (52)
5.1.36. 2-[1-(4-Hydroxybenzyl)-1H-indol-3-yl]-2-oxo-N-
(pyridin-4-yl)acetamide (45)
It was synthesized via route B from 17 using 2-chloromethyl-
pyridine. Yield 24%, mp 201–203 °C. 1H NMR (250 MHz, DMSO-
d6): d 5.75 (s, 2H), 7.34–7.42 (m, 4H), 7.62 (m, 1H), 7.82 (ddd,
J = 7.6, 1.8 Hz, 1H), 7.90 (d, J = 6.0 Hz, 2H), 8.33 (m, 1H), 8.54–
8.57 (m, 3H), 9.04 (s, 1H), 11.15 (s, 1H). ESMS m/z 357.4 (MH+).
Anal. (C21H16N4O2) C, H, N.
It was synthesized by demethylation with boron tribromide17 in
CH2Cl2 from 44. Yield 73%, mp >250 °C. 1H NMR (250 MHz, DMSO-
d6): d 5.46 (s, 2H), 6.73 (d, J = 8.5 Hz, 2H), 7.21 (d, J = 8.4 Hz, 2H),
7.30–7.34 (m, 2H), 7.66–7.68 (m, 1H), 7.86 (d, J = 6.0 Hz, 2H),
8.28–8.30 (m, 1H), 8.52 (d, J = 5.9 Hz, 2H), 8.92 (s, 1H), 9.46 (s,
1H), 11.07 (s, 1H). ESMS m/z 372.4 (MH+). Anal. (C22H17N3O3) C,
H, N.
5.1.44. 2-[1-(4,5-Dichlorobenzyl)-1H-indol-3-yl]-2-oxo-N-
(pyridin-4-yl)acetamide (53)
5.1.37. 2-[1-(4-Aminobenzyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-
4-yl)acetamide (46)
It was synthesized via route B from 17 using 4,5-dichlorobenzyl
chloride. Yield 48%, mp >250 °C. 1H NMR (250 MHz, DMSO-d6): d
5.64 (s, 2H), 7.28 (dd, J = 8.3, 1.3 Hz, 1H), 7.32–7.36 (m, 2H), 7.61
(d, J = 8.3 Hz, 1H), 7.64 (dd, J = 6.7, 2.9 Hz, 1H), 7.68 (d, J = 1.3 Hz,
1H), 7.86 (d, J = 6.0 Hz, 2H), 8.31 (dd, J = 5.5, 2.1 Hz, 1H), 8.52 (d,
J = 6.0 Hz, 2H), 9.04 (s, 1H), 11.09 (s, 1H). ESMS m/z 425.3 (MH+).
Anal. (C22H15Cl2N3O2) C, H, N.
It was synthesized by hydrogenation over Raney nickel18 from
42. Yield 71%, mp 229–233 °C. 1H NMR (250 MHz, DMSO-d6): d
5.16 (s, 2H), 5.36 (s, 2H), 6.51 (d, J = 8.2 Hz, 2H), 7.07 (d,
J = 8.2 Hz, 2H), 7.31–7.33 (m, 2H), 7.67–7.69 (m, 1H), 7.86 (d,
J = 5.5 Hz, 2H), 8.27–8.29 (m, 1H), 8.52 (d, J = 5.5 Hz, 2H), 8.87 (s,
1H), 11.07 (s, 1H). ESMS m/z 371.4 (MH+). Anal. (C22H18N4O2) C,
H, N.
5.1.45. 2-[1-(2,4-Dichlorobenzyl)-1H-indol-3-yl]-2-oxo-N-
(pyridin-4-yl)acetamide (54)
5.1.38. 2-[1-(4-(Acetylamino)benzyl)-1H-indol-3-yl]-2-oxo-N-
(pyridin-4-yl)acetamide (47)
It was synthesized via route B from 17 using 2,4-dichlorobenzyl
chloride. Yield 45%, mp 241–242 °C. 1H NMR (250 MHz, DMSO-d6):
d 5.71 (s, 2H), 6.98 (d, J = 8.4 Hz, 1H), 7.32–7.38 (m, 2H), 7.41 (d,
J = 8.3 Hz, 1H), 7.55 (d, J = 7.9 Hz, 1H), 7.74 (d, J = 1.7 Hz, 1H),
7.85 (d, J = 6.0 Hz, 2H), 8.33 (d, J = 7.6 Hz, 1H), 8.51 (d, J = 6.0 Hz,
2H), 8.92 (s, 1H), 11.09 (s, 1H). ESMS m/z 425.3 (MH+). Anal.
(C22H15Cl2N3O2) C, H, N.
It was synthesized using acetic anhydride19 from 46. Yield 79%,
mp >250 °C. 1H NMR (250 MHz, DMSO-d6): d 2.00 (s, 3H), 5.54 (s,
2H), 7.28–7.34 (m, 4H), 7.53 (d, J = 8.3 Hz, 2H), 7.63 (d, J = 7.4 Hz,
1H), 7.86 (d, J = 5.9 Hz, 2H), 8.30 (d, J = 6.9 Hz, 1H), 8.52 (d,
J = 5.7 Hz, 2H), 8.95 (s, 1H), 9.94 (s, 1H), 11.08 (s, 1H). ESMS m/z
413.4 (MH+). Anal. (C24H20N4O3) C, H, N.
5.1.46. 2-[1-(4-Chloro-3-nitrobenzyl)-1H-indol-3-yl]-2-oxo-N-
(pyridin-4-yl)acetamide (55)
5.1.39. 2-[1-(4-Methylbenzyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-
4-yl)acetamide (48)
It was synthesized via route C from 14 using 4-aminopyridine.
Yield 46%, mp 271–272 °C. 1H NMR (250 MHz, DMSO-d6): d 5.77
(s, 2H), 7.36–7.39 (m, 2H), 7.62 (dd, J = 8.5, 2.0 Hz, 1H), 7.66–7.71
(m, 1H), 7.79 (d, J = 8.5 Hz, 1H), 7.90 (d, J = 5.8 Hz, 2H), 8.19 (d,
J = 2.0 Hz, 1H), 8.34–8.36 (m, 1H), 8.56 (d, J = 5.8 Hz, 2H), 9.12 (s,
1H), 11.15 (s, 1H). ESMS m/z 435.8 (MH+). Anal. (C22H15ClN4O4) C,
H, N.
It was synthesized via route B from 17 using 4-methylbenzyl
chloride. Yield 64%, mp 215–217 °C. 1H NMR (250 MHz, DMSO-
d6): d 2.25 (s, 3H), 5.56 (s, 2H), 7.15 (d, J = 7.9 Hz, 2H), 7.24 (d,
J = 7.9 Hz, 2H), 7.29–7.34 (m, 2H), 7.62 (d, J = 7.1 Hz, 1H), 7.86 (d,
J = 6.0 Hz, 2H), 8.30 (d, J = 8.2 Hz, 1H), 8.52 (d, J = 6.0 Hz, 2H),
8.97 (s, 1H), 11.08 (s, 1H). ESMS m/z 370.4 (MH+). Anal.
(C23H19N3O2) C, H, N.