2-Oxo-2,3-dihydro-1H-indole-5-carbonitrile → HCID 178509446, compound

HRID 1615345Notes

Reaction equation

HRID 1615345 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]#[N:12])[CH:8]=2)[NH:3]1.[N:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]2[C:29]3[C:24](=[CH:25][C:26]([CH:30]=O)=[CH:27][CH:28]=3)[N:23](COCC[Si](C)(C)C)[N:22]=2)=[CH:15][CH:14]=1>>[O:1]=[C:2]1[C:10](=[CH:30][C:26]2[CH:25]=[C:24]3[C:29]([C:21](/[CH:20]=[CH:19]/[C:16]4[CH:15]=[CH:14][N:13]=[CH:18][CH:17]=4)=[N:22][NH:23]3)=[CH:28][CH:27]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]#[N:12])[CH:8]=2)[NH:3]1

Participants

3

Reactant 2

HCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrileHCID 86651957HCID 86651957, compound

Product 1

HCID 178509446HCID 178509446, compound

Procedure

The title compound was synthesized according to the method described in Example A57 from 2-oxoindoline-5-carbonitrile (10 mg, 0.063 mmol) and (E)-3-(2-(pyridin-4-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (25 mg, 0.063 mmol) with a modified purification procedure. The product was precipitated with EtOAc and filtered washing with EtOAc to give 4.5 mg, 30% of a yellow powder which was a 65:35 mixture of (E)/(Z) isomers. 1H NMR (400 MHz, d6-DMSO) δ 14.04, 13.94 (s, 1H), 11.24, 11.22 (s, 1H), 9.01, 8.42 (s, 1H), 8.83 (d, J=5.5 Hz, 2H), 8.50-8.17 (m, 3H), 8.03 (s, 1H), 7.99 (s, 1H), 7.86 (s, 1H), 7.81-7.65 (m, 3H), 7.07, 7.01 (d, J=8.4 Hz, 1H); MS ESI 390.1 [M+H]+, calcd for [C24H15N5O+H]+ 390.14.

Workup

  1. customThe product was precipitated with EtOAc
  2. filtrationfiltered
  3. washwashing with EtOAc

Sources & evidence

ORD record
ord-b00b7be20d624c64a56cf27caf534aab
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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