5-Bromo-2-oxindole → HCID 68755180, compound

HRID 1615278Notes

Reaction equation

HRID 1615278 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][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)[N:22]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[N:21]=2)=[CH:14][CH:13]=1>C(Cl)Cl.CO>[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:15]3[CH:14]=[CH:13][N:12]=[CH:17][CH:16]=3)=[N:21][N:22]2[CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:37])([CH3:38])[CH3:36])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 6111935-Bromo-2-oxindoleHCID 86651957HCID 86651957, compound

Product 1

HCID 68755180HCID 68755180, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared from 5-bromooxindole (36 mg, 0.171 mmol) and (E)-3-(2-(pyridin-4-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (65 mg, 0.171 mmol) as described in Example A57 part B to give, after silica gel column chromatography (Eluent: 98:2 CH2Cl2/MeOH) the title compound as a yellow oil (75 mg, 77%). MS ESI 573.4 [M+H]+, calcd for [C29H29BrN4O2Si+H]+ 573.13.

Workup

  1. customto give

Sources & evidence

ORD record
ord-3a0ce62fb56d45fc87ea698083eff700
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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