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

HRID 1520498노트

반응식

HRID 1520498 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-2994c1ee93a14eeabb322121d854e6b6
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073894B2

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