1,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-one → HCID 178517368, compound

HRID 1615331Notes

Reaction equation

HRID 1615331 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][CH:14]=[C:13](/[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:12]=1>>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13](/[CH:17]=[CH:18]/[C:19]2[C:27]3[C:22](=[CH:23][C:24]([CH:28]=[C:3]4[C:4]5[C:5](=[N:6][CH:7]=[CH:8][CH:9]=5)[NH:1][C:2]4=[O:10])=[CH:25][CH:26]=3)[NH:21][N:20]=2)[CH:12]=1

Participants

3

Reactant 2

HCID 138640951,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-oneHCID 86651944(E)-3-(2-(pyridin-3-yl)vinyl)-1H-indazole-6-carbaldehyde

Product 1

HCID 178517368HCID 178517368, compoundYield 81%

Procedure

The title compound (59 mg, 81%) was synthesized as an orange solid according to the method described for Example A67 (oil temp 75° C., reflux 90 min) using 1H-pyrrolo[2,3-b]pyridin-2(3H)-one (26.8 mg, 0.2 mmol) and (E)-3-(2-(pyridin-3-yl)vinyl)-1H-indazole-6-carbaldehyde (49.8 mg, 0.2 mmol). 1H NMR indicated 5:2 mixture of Z/E isomers. 1H NMR (400 MHz, DMSO-d6) δ 13.60 (s, 1H, NH), 11.30 (s, 1H, NH), 8.95 (s, 1H), 8.91 (d, 1H), 8.47 (d, J=4.4 Hz, 1H), 8.31 (d, J=8.4 Hz, 1H), 8.19 (d, J=7.2 Hz, 1H), 8.13-8.07 (m, 4H), 7.72 (d, J=16.8 Hz, 1H), 7.59 (d, J=17.2 Hz, 1H), 7.42 (dd, J=8.0 Hz, 4.4 Hz, 1H), 7.50 (dd, J=7.2 Hz, 5.6 Hz, 1H); MS ESI 444.3 [M+H]+, calcd for [C22H15N5O+H]+ 366.1.

Workup

  1. customdescribed for Example A67 (oil temp 75° C., reflux 90 min)
  2. addition5:2 mixture of Z/E isomers

Sources & evidence

ORD record
ord-3addad91a525455884dca9ff0846b5b3
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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