Oxindole → (E)-3-((3-((E)-2-(1-methyl-1H-imidazol-2-yl)vinyl)1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-yl)methylene)indolin-2-one

HRID 1615320Notes

Reaction equation

HRID 1615320 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].[CH3:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1/[CH:17]=[CH:18]/[C:19]1[C:27]2[C:22](=[CH:23][C:24]([CH:28]=O)=[CH:25][CH:26]=2)[N:21]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[N:20]=1>>[CH3:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1/[CH:17]=[CH:18]/[C:19]1[C:27]2[C:22](=[CH:23][C:24](/[CH:28]=[C:3]3/[C:2](=[O:10])[NH:1][C:9]4[C:4]/3=[CH:5][CH:6]=[CH:7][CH:8]=4)=[CH:25][CH:26]=2)[N:21]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:35])[CH3:36])[N:20]=1

Participants

3

Reactant 2

HCID 321710OxindoleHCID 86651978(E)-3-(2-(1-methyl-1H-imidazol-2-yl)vinyl)-1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-indazole-6-carbaldehyde

Product 1

HCID 69811124(E)-3-((3-((E)-2-(1-methyl-1H-imidazol-2-yl)vinyl)1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-yl)methylene)indolin-2-one

Procedure

Synthesized according to the method of Example A19, utilizing indolin-2-one (14.5 mg, 0.11 mmol) and (E)-3-(2-(1-methyl-1H-imidazol-2-yl)vinyl)-1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-indazole-6-carbaldehyde (41.6 mg, 0.11 mmol). The crude mixture was concentrated under reduced pressure and purified by prepTLC (SiO2 10% MeOH/DCM) to provide the title compound to as a yellow material (35.4 mg, 65%); MS ESI 498.4 [M+H]+, calcd for [C28H31N5O2Si+H]+ 498.7.

Workup

  1. customSynthesized
  2. concentrationThe crude mixture was concentrated under reduced pressure
  3. custompurified by prepTLC (SiO2 10% MeOH/DCM)

Sources & evidence

ORD record
ord-cfc01ce84d6d41ab99ff0d78bd0f63c2
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

Loading…