6-Bromoindole-3-carbaldehyde → 6-Bromo-3-methyl-1H-indole
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=O)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:11])=[CH:7][NH:8]2)=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 6-bromo-1H-indole-3-carbaldehyde (300 mg, 1.34 mmol) in THF (10 mL) was added LiAlH4 (100 mg, 2.63 mmol) at 0° C. The mixture was heated to 70° C. and stirred for 4 h at this temperature. Upon cooling, the reaction solution was quenched with 40% of NaOH and filtered and the filtrate concentrated to give crude product which was used in next step without further purification. LCMS (m/z): 210.1 [M+H]+.
Workup
- temperatureUpon cooling
- customthe reaction solution was quenched with 40% of NaOH
- filtrationfiltered
- concentrationthe filtrate concentrated
- customto give crude product which
- customwas used in next step without further purification
Sources & evidence
- ORD record
- ord-8c9f69d94425416db2fd49ed99654998
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906900B2
Reaction notes
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