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

HRID 1454210ノート

反応式

HRID 1454210 の反応式
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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
122 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4b2bb2f369af442b803081ec5df242f7
出典データセット
uspto-grants-2009_01
特許番号
US07476764B2

反応ノート

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