Dichloromethane → Ethyl 3-(isopropylamino)benzoate

HRID 400529

반응식

HRID 400529 반응식
P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH:21]([NH2:24])([CH3:23])[CH3:22].ClCCl>C(COC)OC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:21]([NH:24][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])([CH3:23])[CH3:22]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 6363IsopropylamineHCID 62657Potassium Phosphate, TribasicHCID 90488Ethyl 3-bromobenzoate

생성물 1

HCID 43087836Ethyl 3-(isopropylamino)benzoate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매2회

반응 조건

온도
160 °C

실험 절차

Potassium phosphate (1.38 g, 6.5 mmol), palladium(II) acetate (56 mg, 0.25 mmol), and (R)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine (139 mg, 0.25 mmol) were combined in a microwave tube under nitrogen. Ethyl 3-bromobenzoate (1.145 g, 5 mmol) in dimethoxyethane (2 mL) and isopropylamine (385 mg, 6.5 mmol) in dimethoxyethane (2 mL) were added. The tube was filled with nitrogen again. The tube was then capped, and the reaction mixture was heated in a microwave oven (Biotage Initiator™ 2.0, 0 to 100 watts) with stirring at 160° C. for 70 minutes. Then dichloromethane was added, and the crude mixture was filtered. The filtrate was concentrated. The residue was purified by chromatography on silica gel (hexane/ethyl acetate=7:1) to give ethyl 3-(isopropylamino)benzoate.

후처리

  1. additionThe tube was filled with nitrogen again
  2. customThe tube was then capped
  3. temperaturethe reaction mixture was heated in a microwave oven (Biotage Initiator™ 2.0, 0 to 100 watts)
  4. filtrationthe crude mixture was filtered
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified by chromatography on silica gel (hexane/ethyl acetate=7:1)

출처 및 근거

ORD 기록
ord-298c13724bb8494f8703f9520bb511b1
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741899B2

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