1,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-one → HCID 178517369, compound

HRID 1615310Notes

Reaction equation

HRID 1615310 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][C:2]1=[O:10].[N:11]1[CH:16]=[CH:15][C:14]([CH:17]=[CH:18][C:19]2[C:27]3[C:22](=[CH:23][C:24]([CH:28]=O)=[CH:25][CH:26]=3)[NH:21][N:20]=2)=[CH:13][CH:12]=1>>[N:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]2[C:27]3[C:22](=[CH:23][C:24](/[CH:28]=[C:3]4/[C:2](=[O:10])[NH:1][C:5]5[C:4]/4=[CH:9][CH:8]=[CH:7][N:6]=5)=[CH:25][CH:26]=3)[NH:21][N:20]=2)=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 138640951,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-oneHCID 86651972HCID 86651972, compound

Product 1

HCID 178517369HCID 178517369, compoundYield 87.6%

Procedure

The title compound (64 mg, 64%) was synthesized as orange red solid according to the method described for Example A11B from 1H-pyrrolo[2,3-b]pyridin-2(3H)-one (26.8 mg, 0.2 mmol) and E)-3-(2-(pyridin-4-yl)vinyl)-1H-indazole-6-carbaldehyde (49.8 mg, 0.2 mmol). 1H NMR (400 MHz, DMSO-d6) δ 13.60 (s, 1H, NH), 11.28 (s, 1H, NH), 8.57 (d, J=5.6 Hz, 2H), 8.39 (d, J=8.4 Hz, 1H), 8.12 (d, J=4.8 Hz, 1H), 7.95 (s, 2H), 7.90 (d, J=6.4 Hz, 1H, partially overlapping with the peak at 7.87 ppm), 7.87 (d, J=16.4 Hz, 1H, partially overlapping with the peak at 7.90 ppm), 7.71 (d, J=5.6 Hz, 2H), 7.57 (d, J=8.0 Hz, 1H, partially overlapping with the peak at 7.56 ppm), 7.56 (d, J=16.4 Hz, 1H, partially overlapping with the peak at 7.57 ppm), 6.91 (dd, J=7.6 Hz, 5.2 Hz, 1H); MS ESI 366.1 [M+H]+, calcd for [C22H15N5O+H]+ 366.1.

Sources & evidence

ORD record
ord-549fe36cab774c8c92f8511591f00de9
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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