5-Bromo-2-oxindole → HCID 178517019, compound

HRID 1615358Notes

Reaction equation

HRID 1615358 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](/[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:13]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:29][C:25]1[CH:24]=[C:23]2[C:28]([C:20](/[CH:19]=[CH:18]/[C:14]3[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=3)=[N:21][NH:22]2)=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 6111935-Bromo-2-oxindoleHCID 86651944(E)-3-(2-(pyridin-3-yl)vinyl)-1H-indazole-6-carbaldehyde

Product 1

HCID 178517019HCID 178517019, compoundYield 83%

Procedure

The title compound (E:Z=1:4, 73 mg, 83%) was synthesized as a dark yellow solid according to the method described for Example A67 (oil temp 75° C., reflux 2 h) using 5-bromoindolin-2-one (44.5 mg, 0.21 mmol) and (E)-3-(2-(pyridin-3-yl)vinyl)-1H-indazole-6-carbaldehyde (49.8 mg, 0.2 mmol). 1H NMR (400 MHz, DMSO-d6): δ 13.60 (s, 1H), 10.84 (s, 1H), 8.99 (s, 1H), 8.91 (s, 1H), 8.48 (d, J=4.4 Hz, 1H), 8.30 (d, J=8.4 Hz, 1H), 8.19 (d, J=8.0 Hz, 1H), 8.16-8.10 (m, 3H), 8.04 (s, 1H), 7.71 (d, J=16.8 Hz, 1H), 7.59 (d, J=17.2 Hz, 1H), 7.43 (dd, J=7.6 Hz, J=4.8 Hz, 1H), 7.39 (dd, J=8.0 Hz, J=1.2 Hz, 1H); MS ESI 443.3 [M+H]+, calcd for [C23H15BrN4O+H]+ 443.1.

Workup

  1. customdescribed for Example A67 (oil temp 75° C., reflux 2 h)

Sources & evidence

ORD record
ord-7ea3f33895174c2491f4deee3910fab7
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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