Methanol → 2-methylaminomethyl-1H-indole-3-carbonitrile

HRID 2097101Notes

Reaction equation

HRID 2097101 reaction equation
[CH3:1][NH2:2].CO.[CH:5]([C:7]1[NH:8][C:9]2[C:14]([C:15]=1[C:16]#[N:17])=[CH:13][CH:12]=[CH:11][CH:10]=2)=O.[BH4-].[Na+]>O>[CH3:1][NH:2][CH2:5][C:7]1[NH:8][C:9]2[C:14]([C:15]=1[C:16]#[N:17])=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

6

Reactant 4

HCID 887MethanolHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 592775632-formyl-1H-indole-3-carbonitrile

Product 1

HCID 592775892-methylaminomethyl-1H-indole-3-carbonitrileYield 75.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Methylamine (6.2 mL, 49.4 mmol, 33% in EtOH) was added to a MeOH (50 mL) solution of 2-formyl-1H-indole-3-carbonitrile (2.80 g, 16.5 mmol) at 0° C. Upon stirring for 5 h at 0° C., NaBH4 (740 mg, 19.8 mmol) was added to the solution and the stirring was continued for 16 h. The mixture was diluted with water, extracted with methylene chloride; the organic layer was dried and evaporated. The crude residue was subjected to chromatography (1-5% MeOH in methylene chloride). The desired fractions were collected and concentrated; the residue was recrystallized from a methylene chloride/hexane mixture to afford the title compound (2.30 g, 75%). 1H NMR (300 MHz, DMSO-d6, 8): 7.54 (m, 1H), 7.48 (m, 1H), 7.21 (m, 2H), 3.93 (s, 2H), 2.31 (s, 3H). MS (ESI): m/e 186 (M+H)+.

Workup

  1. waitthe stirring was continued for 16 h
  2. extractionextracted with methylene chloride
  3. customthe organic layer was dried
  4. customevaporated
  5. customThe desired fractions were collected
  6. concentrationconcentrated
  7. customthe residue was recrystallized from a methylene chloride/hexane mixture

Sources & evidence

ORD record
ord-2ef0626dee644e3a879d7c918a7109c3
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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