Oxindole → HCID 178517052, compound

HRID 1615363Notes

Reaction equation

HRID 1615363 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[C: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]([C:17]#[C: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:9]5[C:4]/4=[CH:5][CH:6]=[CH:7][CH:8]=5)=[CH:25][CH:26]=3)[NH:21][N:20]=2)[CH:12]=1

Participants

3

Reactant 2

HCID 321710OxindoleHCID 178519313HCID 178519313, compound

Product 1

HCID 178517052HCID 178517052, compoundYield 83%

Procedure

The title compound (30 mg, 83%) was synthesized as a yellow solid according to the method described for Example A67 (oil temp 75° C., reflux 2 h) using indolin-2-one (13.3 mg, 0.1 mmol) and 3-(pyridin-3-ylethynyl)-1H-indazole-6-carbaldehyde (24.7 mg, 0.1 mmol). 1H NMR (400 MHz, DMSO-d6) δ 13.80 (s, 1H), 10.64 (s, 1H), 8.90 (s, 1H), 9.64 (d, J=4.4 Hz, 1H), 8.12 (d, J=8.0 Hz, 1H), 8.03 (d, J=8.0 Hz, 1H), 7.96 (s, 1H), 7.80 (s, 1H), 7.60-7.50 (m, 3H), 7.24 (t, J=7.8 Hz, 1H), 6.89 (d, J=7.6 Hz, 1H) 6.84 (t, J=7.8 Hz, 1H); MS ESI 363.1 [M+H]+, calcd for [C23H14N4O+H]+ 363.1.

Workup

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

Sources & evidence

ORD record
ord-52a75fcab08248779a7c6a9668234ad7
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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