Water → 1-(5-(2-fluorophenyl)-1H-pyrrol-3-yl)-N-methylmethanamine

HRID 1051001Notes

Reaction equation

HRID 1051001 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][CH:11]=[C:10]([CH:13]=O)[CH:9]=1.[BH4-].[Na+].O.[CH3:18][NH2:19]>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][CH:11]=[C:10]([CH2:13][NH:19][CH3:18])[CH:9]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 469085935-(2-Fluorophenyl)-1H-pyrrole-3-carboxaldehyde

Product 1

HCID 901686941-(5-(2-fluorophenyl)-1H-pyrrol-3-yl)-N-methylmethanamine

Procedure

5-(2-Fluorophenyl)-1H-pyrrol-3-carboxaldehyde 1d (1.89 g, 10 mmol, prepared by a known method disclosed in “Journal of Medicinal Chemistry”, 2012, 55(9), 4446-4456) was dissolved in 20 mL of methylamine, and the reaction solution was stirred for 1 h. Sodium borohydride (1.14 g, 30 mmol) was added and continuously stirred for 1 h. 10 mL of water were added to the reaction solution, and the reaction solution was concentrated under reduced pressure to obtain the title product 1-(5-(2-fluorophenyl)-1H-pyrrol-3-yl)-N-methylmethanamine 1e (2.0 g, a yellow oil), which was used directly in the next step.

Workup

  1. stirringcontinuously stirred for 1 h
  2. concentrationthe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2e8aa4c858c547eb8a8acded736bda9d
Source dataset
uspto-grants-2016_07
Patent number
US09388133B2

Reaction notes

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