4-Aminoindolin-2-one → HCID 17989256, compound

HRID 1869339Notes

Reaction equation

HRID 1869339 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=O)=[C:4]([O:20][CH3:21])[CH:3]=1.[NH2:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH2:25][C:26](=[O:32])[NH:27]2>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:18])([CH3:19])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=[N:22][C:23]2[CH:31]=[CH:30][CH:29]=[C:28]3[C:24]=2[CH2:25][C:26](=[O:32])[NH:27]3)=[C:4]([O:20][CH3:21])[CH:3]=1

Participants

4

Reactant 2

HCID 122374724-Aminoindolin-2-oneHCID 17985040HCID 17985040, compound

Product 1

HCID 17989256HCID 17989256, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

300 mg (0.812 mmol) of 4-(4-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentanal is stirred in 1.5 ml of glacial acetic acid with 120.4 mg (0.812 mmol) of 4-amino-1,3-dihydroindol-2-one over a weekend at room temperature. The reaction mixture is evaporated until a dry state is reached, and the residue is put on a Flashmaster column. 235.9 mg (58.1%) of the desired imine is isolated.

Workup

  1. customThe reaction mixture is evaporated until a dry state

Sources & evidence

ORD record
ord-99cf62dd1b6843c2b4c897b4f3c87f9b
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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