5-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one → HCID 178517360, compound

HRID 1615327Notes

Reaction equation

HRID 1615327 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.[N:12]1[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]2[C:28]3[C:23](=[CH:24][C:25]([CH:29]=O)=[CH:26][CH:27]=3)[NH:22][N:21]=2)=[CH:14][CH:13]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:29][C:25]3[CH:24]=[C:23]4[C:28]([C:20](/[CH:19]=[CH:18]/[C:15]5[CH:14]=[CH:13][N:12]=[CH:17][CH:16]=5)=[N:21][NH:22]4)=[CH:27][CH:26]=3)[C:9](=[O:11])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 155040625-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-oneHCID 86651943HCID 86651943, compound

Product 1

HCID 178517360HCID 178517360, compoundYield 72%

Procedure

The title compound (64 mg, 64%) was synthesized as a greenish yellow solid according to the method described for Example A67 (oil temp 75° C., reflux 2 h) using 5-bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (42.6 mg, 0.2 mmol) and (E)-3-(2-(pyridin-4-yl)vinyl)-1H-indazole-6-carbaldehyde (49.8 mg, 0.2 mmol). 1H NMR indicated 7:6 mixture of E/Z isomers. 1H NMR (400 MHz, DMSO-d6) δ 8.57 (d, J=5.2 Hz, 2H), 8.34 (d, J=8.4 Hz, 1H), 8.26 (d, 1H), 8.22 (s, 1H), 8.12 (d, J=8.8 Hz, 1H), 8.03 (s, 1H), 7.93 (d, 1H), 7.89 (d, J=16.8 Hz, 1H), 7.72 (t, J=4.8 Hz, 2H), 7.55 (d, J=16.0 Hz, 1H); MS ESI 444.3 [M+H]+, calcd for [C22H14BrN5O+H]+ 444.0.

Workup

  1. customdescribed for Example A67 (oil temp 75° C., reflux 2 h)
  2. addition7:6 mixture of E/Z isomers

Sources & evidence

ORD record
ord-685e29bdb4b94d929514052f2d1a0c8c
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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