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

HRID 525567노트

반응식

HRID 525567 반응식
[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

참가 물질

5

반응물 2

HCID 5003444Sodium cyanoborohydrideHCID 178482620HCID 178482620, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-071e5905738f4de49c9f2a0208af727c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340564B2

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