Triethylamine → 2-Bromo-N-(3,4-dimethyl-phenyl)-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

HRID 1094368

反応式

HRID 1094368 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][CH2:11][C:12]2[CH:13]=[N:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C(N(CC)CC)C.[Br:29][CH2:30][C:31](Cl)=[O:32]>C(OCC)C.CC(OC)(C)C>[Br:29][CH2:30][C:31]([N:9]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1)[CH2:10][CH2:11][C:12]1[CH:13]=[N:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=1)=[O:32]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 89602Bromoacetyl chloride2 回HCID 58007591(3,4-Dimethyl-phenyl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-amine

生成物 1

HCID 580076022-Bromo-N-(3,4-dimethyl-phenyl)-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide収率 43%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

A solution of (3,4-dimethyl-phenyl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-amine (220 mg, 0.75 mmol) in diethylether (2 mL) was cooled to 0° C. and triethylamine (114 μL, 0.82 mmol) and bromoacetyl chloride (81 μL, 0.97 mmol) were added. After stirring for 15 min. at this temperature the ice bath was removed and the suspension was stirred for 2 h at ambient temperature. Further bromoacetyl chloride (16 μL, 0.2 mmol) was added and the resulting suspension was stirred for 1 h at this temperature. It was diluted with TBME (10 mL) and washed with water (15 mL) and brine (15 mL). The combined aqueous layers were extracted with TBME (15 mL) and the combined organic layers dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 70:30) afforded the title compound (134 mg, 43%) as a light brown oil. MS m/e: 417.1 [M+H]+.

後処理

  1. customwas removed
  2. stirringthe resulting suspension was stirred for 1 h at this temperature
  3. washwashed with water (15 mL) and brine (15 mL)
  4. extractionThe combined aqueous layers were extracted with TBME (15 mL)
  5. dry with materialthe combined organic layers dried over sodium sulfate
  6. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 70:30)

出典と根拠

ORDレコード
ord-1689b8c1754f4310bc5d7f48edbf9a13
出典データセット
uspto-grants-2012_03
特許番号
US08133909B2

関連ノート

読み込み中…