6-Bromo-3-hydroxy-3-methylindolin-2-one → 6-Bromo-3-methyl-1H-indole

HRID 1960118

Reaction equation

HRID 1960118 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](O)([CH3:12])[C:7](=O)[NH:8]2)=[CH:4][CH:3]=1>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 665802586-Bromo-3-hydroxy-3-methylindolin-2-one

Product 1

HCID 534029586-Bromo-3-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-bromo-3-hydroxy-3-methyl-1,3-dihydro-2H-indol-2-one (0.25 g, 1.0 mmol) and BH3—S(CH3)2 (5.16 mL. 1.0 M, 5.16 mmol) in THF (20 mL) was heated at 60° C. The reaction was quenched with MeOH. Volatiles were removed. Chromatography over silica eluting with 4:1 hexane:EtOAc afforded the title compound. LC-MS: calculated for C9H8BrN: 210.07, observed m/e 211.0 (M+H)+ (Rt 1.14 min).

Workup

  1. customThe reaction was quenched with MeOH
  2. customVolatiles were removed

Sources & evidence

ORD record
ord-ec0511236f004791ba2484d0edcac0b6
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Linked notes

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