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

HRID 1520498ノート

反応式

HRID 1520498 の反応式
[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

参加物

5

反応物 2

HCID 5003444Sodium cyanoborohydrideHCID 178482620HCID 178482620、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2994c1ee93a14eeabb322121d854e6b6
出典データセット
uspto-grants-2015_07
特許番号
US09073894B2

反応ノート

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