Hydrochloric Acid → Methyl 3-acetyl-5-((1-(4-fluorophenyl)ethyl)-carbamoyl)benzoate

HRID 1454210노트

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HRID 1454210 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12](=[O:23])[NH:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH:24]([O:26]CCCC)=[CH2:25].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:24]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12](=[O:23])[NH:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:26])[CH3:25]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 57529327Methyl 3-bromo-5-((1-(4-fluorophenyl)ethyl)-carbamoyl)benzoate

생성물 1

HCID 57529315Methyl 3-acetyl-5-((1-(4-fluorophenyl)ethyl)-carbamoyl)benzoate수율 65.4%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
122 °C

실험 절차

A mixture of methyl 3-bromo-5-((1-(4-fluorophenyl)ethyl)-carbamoyl)benzoate (880 mg, 2.32 mmol), 1-(vinyloxy)butane (464.7 mg, 0.6 mL, 4.64 mmol), palladium acetate (16.0 mg, 0.070 mmol), DPPP (63.1 mg, 0.0153 mmol) and potassium carbonate (382 mg, 2.78 mmol) in DMF (2.5 mL) and H2O (0.3 mL) in a Smith process vial was heated at 122° C. in microwave for 3 h. The reaction mixture was cooled down to RT and hydrolyzed by addition of 5% HCl slowly. The reaction mixture was worked up by extraction with ethyl acetate and concentration under vacuum. The crude mixture was purified by reverse phase prep HPLC to give the title compound (520 mg, 65.4% yield): HPLC retention time: 1.88 min (method A). MS (ESI) (M+H)+ 343.00.

후처리

  1. extractionThe reaction mixture was worked up by extraction with ethyl acetate and concentration under vacuum
  2. customThe crude mixture was purified by reverse phase prep HPLC

출처 및 근거

ORD 기록
ord-4b2bb2f369af442b803081ec5df242f7
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476764B2

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