6-Bromoindole-3-carbaldehyde → 6-Bromo-3-methyl-1H-indole

HRID 1051489

Reaction equation

HRID 1051489 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]=1

Participants

4

Reactant 2

HCID 27948306-Bromoindole-3-carbaldehydeHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. temperatureUpon cooling
  2. customthe reaction solution was quenched with 40% of NaOH
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. customto give crude product which
  6. customwas used in next step without further purification

Sources & evidence

ORD record
ord-1f0e6728a63b4fef9cfa2b223f47e713
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Linked notes

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