Acetyl chloride → HCID 68283887, 화합물

HRID 1527267노트

반응식

HRID 1527267 반응식
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[CH:7][N:6]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:19](Cl)(=[O:21])[CH3:20]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:19](=[O:21])[CH3:20])[N:6]=1

참가 물질

5

반응물 3

HCID 6367Acetyl chloride2회HCID 6451240Aluminum(III) Chloride2회HCID 21265856HCID 21265856, 화합물

생성물 1

HCID 68283887HCID 68283887, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of imidazo[1,5-a]pyridin-3-yl-acetic acid methyl ester (1.38 g, 7.26 mmol) in CH2Cl2 (50 mL) was added to a suspension of AlCl3 (2.9 g, 21.77 mmol) in CH2Cl2 (115 mL) and the mixture was stirred at RT for 30 min under nitrogen atmosphere. Acetyl chloride (1.55 mL, 21.77 mmol) was subsequently added dropwise and the mixture was further stirred overnight. AlCl3 (1.94 g, 14.51 mmol) and 15 min later acetyl chloride (1.04 mL, 14.51 mmol) were added and stirring was continued overnight to complete the reaction. The reaction mixture was cooled with at 0° C. and carefully quenched by cautious addition of MeOH (35 mL). Solvents were evaporated under reduced pressure and the crude residue was purified by flash column chromatography on silica gel (eluent: CH2Cl2 to CH2Cl2/MeOH 94:6). TLC, Rf (CH2Cl2/MeOH 9:1)=0.60; MS (UPLC/MS): 233.1 [M+H]+, 255.1 [M+Na]+, 487.1 [2M+Na]+; tR (HPLC conditions f): 1.27 min.

후처리

  1. waitthe mixture was further stirred overnight
  2. stirringstirring
  3. waitwas continued overnight
  4. customthe reaction
  5. temperatureThe reaction mixture was cooled with at 0° C.
  6. customcarefully quenched by cautious addition of MeOH (35 mL)
  7. customSolvents were evaporated under reduced pressure
  8. customthe crude residue was purified by flash column chromatography on silica gel (eluent: CH2Cl2 to CH2Cl2/MeOH 94:6)
  9. custom1.27 min.

출처 및 근거

ORD 기록
ord-be9343d20c66407d939f0796829fb035
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085555B2

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