Sodium Carbonate → 5-(2-Oxopyrrolidin-1-yl)-biphenyl-3-carboxylic Acid Methyl Ester

HRID 1612436노트

반응식

HRID 1612436 반응식
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6](Br)[CH:5]=1.C([O-])([O-])=O.[Na+].[Na+].[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>COCCOC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:9]=1)=[O:17]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 22253055Methyl 3-bromo-5-(2-oxopyrrolidin-1-yl)benzoate

생성물 1

HCID 695897705-(2-Oxopyrrolidin-1-yl)-biphenyl-3-carboxylic Acid Methyl Ester수율 33.1%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
85 °C

실험 절차

To 3-bromo-5-(2-oxopyrrolidin-1-yl)benzoic acid methyl ester (D9) (70 mg, 0.235 mmol) in DME (2 ml) was added Na2CO3 (290 μl, 2M, 0.588 mmol), benzeneboronic acid (29 mg, 0.235 mmol) and Pd(OAc)2 (3 mg, 0.013 mmol). The mixture was stirred at 85° C. for 2 days. The reaction mixture was cooled down, filtrated through celite and evaporated in vacuo. The product was purified by column chromatography (PE:EtOAc=3:1) which yielded D10 (23 mg).

후처리

  1. temperatureThe reaction mixture was cooled down
  2. filtrationfiltrated through celite
  3. customevaporated in vacuo
  4. customThe product was purified by column chromatography (PE:EtOAc=3:1) which

출처 및 근거

ORD 기록
ord-95a34c1f03144faaa63971fadbafdd6d
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06992103B2

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