Pyridine → 7-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-c]pyridine

HRID 639527노트

반응식

HRID 639527 반응식
CO[C:3](=O)[NH:4][C:5]1[C:6]([Cl:15])=[N:7][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:10]=1.N1C=CC=C[CH:18]=1.ClC(OC)=O.NC1C(Cl)=NC(C(F)(F)F)=CC=1>ClCCl>[Cl:15][C:6]1[N:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[C:10]2[CH:18]=[CH:3][NH:4][C:5]=12

참가 물질

6

반응물 4

HCID 1049Pyridine2회HCID 6586Methyl chloroformate2회HCID 27376462-Chloro-6-(trifluoromethyl)pyridin-3-amineHCID 86614143(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-carbamic acid methyl ester

생성물 1

HCID 717428487-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-c]pyridine수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-carbamic acid methyl ester: Pyridine (3.98 g, 50.4 mmol) and methyl chloroformate (2.62 g, 27.7 mmol) were added at 0° C. to a solution of 3-amino-2-chloro-6-trifluoromethylpyridine (4.95 g, 25.2 mmol) in dichloromethane (100 ml). The reaction mixture was stirred for 18 h at RT, then cooled to 0° C. and treated with pyridine (3.98 g, 50.4 mmol) and methyl chloroformate (0.95 g, 10 mmol). The reaction mixture was stirred for 24 h at RT and 2.5 h at reflux, then partitioned between ethyl acetate and 10% aq. sodium hydrogencarbonate solution. The organic layer was washed with 10% aq. citric acid solution and brine, dried (MgSO4), and evaporated. Chromatography of the residue (SiO2, heptane/ethyl acetate 4:1) afforded the title compound (4.47 g, 70%). White solid, MS (EI) 219.1 (100), 254.1 (28, M+).

후처리

  1. temperaturecooled to 0° C.
  2. stirringThe reaction mixture was stirred for 24 h at RT and 2.5 h
  3. temperatureat reflux
  4. custompartitioned between ethyl acetate and 10% aq. sodium hydrogencarbonate solution
  5. washThe organic layer was washed with 10% aq. citric acid solution and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

출처 및 근거

ORD 기록
ord-b74460bd6c1a4a8d93cdd5c94a57059c
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691876B2

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