Sodium cyanoborohydride → [1-(5-Bromo-pyridin-2-yl)-2,2,2-trifluoro-ethyl]-methyl-amine

HRID 525567Notes

Reaction equation

HRID 525567 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](/[C:8](=[N:13]\[CH3:14])/[C:9]([F:12])([F:11])[F:10])=[N:6][CH:7]=1.C([BH3-])#N.[Na+]>CO.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([NH:13][CH3:14])[C:9]([F:10])([F:11])[F:12])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 178482620HCID 178482620, compound

Product 1

HCID 86695450[1-(5-Bromo-pyridin-2-yl)-2,2,2-trifluoro-ethyl]-methyl-amineYield 74.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of [1-(5-Bromo-pyridin-2-yl)-2,2,2-trifluoro-eth-(E)-ylidene]-methyl-amine (0.1 g, 0.375 mmol) in methanol (5 mL) is added sodium cyano borohydride (0.027 g, 0.449 mmol) at 0° C. then stirred room temperature for 2 h. Reaction mixture is diluted with saturated sodium bicarbonate solution and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by column chromatography eluting in 10% ethyl acetate in hexane to give the crude title compound (0.075 g, crude). 1H-NMR (400 MHz, DMSO) δ: 2.21 (d, J=5.32 Hz, 3H), 3.04 (m, 1H), 4.46 (m, 1H), 7.74 (d, J=8.24 Hz, 1H), 8.87 (dd, J1=2.4 Hz, J2=8.28 Hz, 1H), 8.48 (d, J1=2.36 Hz, 1H). LC-MS (m/z): [M+H]=271.2.

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialOrganic layer is dried over sodium sulphate, solvent
  4. customis evaporated in vacuo
  5. custompurified by column chromatography
  6. washeluting in 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-071e5905738f4de49c9f2a0208af727c
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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