5-Methoxyoxindole → HCID 178487104, compound

HRID 1615335Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2.[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:42])/[CH:21]=[CH:22]/[C:23]2[C:31]3[C:26](=[CH:27][C:28]([CH:32]=O)=[CH:29][CH:30]=3)[N:25](COCC[Si](C)(C)C)[N:24]=2)[CH2:16][CH2:15]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[CH:32][C:28]1[CH:27]=[C:26]2[C:31]([C:23](/[CH:22]=[CH:21]/[C:20]([N:17]3[CH2:16][CH2:15][N:14]([CH3:13])[CH2:19][CH2:18]3)=[O:42])=[N:24][NH:25]2)=[CH:30][CH:29]=1

Participants

Reactant 2

HCID 15142865-Methoxyoxindole

HCID 86651983HCID 86651983, compound

Product 1

HCID 178487104HCID 178487104, compoundYield 9.7%

Procedure

The synthetic method followed that described in Example A66 starting from 5-methoxyoxindole (10 mg, 0.0583 mmol) and (E)-3-(3-(4-methylpiperazin-1-yl)-3-oxoprop-1-enyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (25 mg, 0.0.0583 mmol) to give 2.5 mg of the title compound as an 85:15 mixture of (E)/(Z) isomers. 1H NMR (400 MHz, CD3OD) 8.95, 7.80 (s, 1H), 8.21-8.16 (m, 1H), 7.97-7.87 (m, 2H), 7.59 (d, J=7.52 Hz, 1H), 7.45 (d, J=15.7 Hz, 1H), 7.32, 7.22 (s, 1H), 6.85 (s, 2H), 3.84, 3.63 (s, 3H), 3.90-3.75 (m, 4H), 2.62-2.48 (br. s, 4H), 2.34 (s, 3H); MS ESI 444.2 [M+H]+, calcd for [C25H25N5O3+H]+ 444.20.

Sources & evidence

ORD record: ord-0af2365777aa45469317e50c4fa4e3b7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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