Dichloromethane → Ethyl 3-(isopropylamino)benzoate

HRID 400529

反応式

HRID 400529 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 43087836Ethyl 3-(isopropylamino)benzoate

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
160 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-298c13724bb8494f8703f9520bb511b1
出典データセット
uspto-grants-2014_06
特許番号
US08741899B2

関連ノート

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