Acetyl chloride → HCID 68283887, compound

HRID 1527267Notes

Reaction equation

HRID 1527267 reaction equation
[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

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 6451240Aluminum(III) Chloride2×HCID 21265856HCID 21265856, compound

Product 1

HCID 68283887HCID 68283887, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-be9343d20c66407d939f0796829fb035
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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