Hydrochloric Acid → HCID 57529321, 화합물

HRID 1454191노트

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HRID 1454191 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12](=[O:18])[N:13]([CH3:17])[CH2:14][CH2:15][CH3:16])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH:19]([O:21]CCCC)=[CH2:20].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:19]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12](=[O:18])[N:13]([CH3:17])[CH2:14][CH2:15][CH3:16])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:21])[CH3:20]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 57529325Methyl 3-bromo-5-(methyl(propyl)carbamoyl)benzoate

생성물 1

HCID 57529321HCID 57529321, 화합물수율 63.1%

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-(methyl(propyl)carbamoyl)benzoate (314 mg, 1.0 mmol), 1-(vinyloxy)butane (200.4 mg, 0.26 mL, 2.0 mmol), palladium acetate (6.68 mg, 0.030 mmol), DPPP (27.2 mg, 0.066 mmol) and potassium carbonate (166 mg, 1.2 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 (175 mg, 63% yield): HPLC retention time: 1.58 min (method A). MS (ESI) (M+H)+ 278.19.

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-999ee1499afc4e6fa61cc8c9b66d6719
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476764B2

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