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

HRID 1094368

반응식

HRID 1094368 반응식
[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]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 89602Bromoacetyl chloride2회HCID 58007591(3,4-Dimethyl-phenyl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-amine

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 15413tert-Butyl methyl ether용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-1689b8c1754f4310bc5d7f48edbf9a13
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133909B2

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