5-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one → HCID 178517361, compound

HRID 2383570Notes

Reaction equation

HRID 2383570 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:10][C:9](=[O:11])[NH:8][C:5]2=[N:6][CH:7]=1.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH:21]=O)[CH:19]=2)[CH:14]=[N:13]1>>[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH:21]=[C:10]3[C:4]4[C:5](=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=4)[NH:8][C:9]3=[O:11])[CH:19]=2)[CH:14]=[N:13]1

Participants

3

Reactant 2

HCID 155040625-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-oneHCID 185383681H-Indazole-6-carbaldehyde

Product 1

HCID 178517361HCID 178517361, compoundYield 146.6%

Procedure

The title compound (50 mg, 95%) was synthesized as a green solid according to the method described for (E/Z)-3-((3-iodo-1H-indazol-6-yl)methylene)-5-methoxyindolin-2-one using 5-bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (21.3 mg, 0.1 mmol) and 1H-indazole-6-carbaldehyde (14.6 mg, 0.1 mmol). 1H NMR indicated 56:44 mixture of E/Z isomers. E isomer: 1H NMR (400 MHz, DMSO-d6) δ 13.38 (s, 1H, NH), 11.45 (s, 1H, NH), 8.38 (d, J=2.0 Hz, 1H), 8.25 (d, J=2.0 Hz, 1H), 8.19 (s, 1H), 8.01 (s, 1H), 7.93 (s, 1H), 7.90 (d, J=2.0 Hz, 1H), 7.45 (dd, J=8.4 Hz, 2.0 Hz, 1H); Z isomer: δ 13.46 (s, 1H, NH), 11.45 (s, 1H, NH), 8.94 (s, 1H), 8.21 (d, J=2.0 Hz, 1H), 8.19 (s, 1H), 8.15 (s, 1H), 7.99 (dd, J=8.8 Hz, 1.6 Hz, 1H), 7.94 (d, J=8.4 Hz, 1H), 7.85 (d, J=8.0 Hz, 1H); MS ESI 341.0 [M+H]+, calcd for [C15H9BrN4O+H]+ 341.1.

Workup

  1. addition56:44 mixture of E/Z isomers

Sources & evidence

ORD record
ord-2ea16f167e1143e48417e3d0798f0bbe
Source dataset
uspto-grants-2012_09
Patent number
US08263596B2

Reaction notes

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