Methyl iodide → 4-Bromo-2-[(cyclopropyl-methylamino)-methyl]-benzoic acid isopropyl ester

HRID 1765828노트

반응식

HRID 1765828 반응식
[CH:1]([O:4][C:5](=[O:18])[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[CH2:13][NH:14][CH:15]1[CH2:17][CH2:16]1)([CH3:3])[CH3:2].[C:19](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH:1]([O:4][C:5](=[O:18])[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[CH2:13][N:14]([CH:15]1[CH2:16][CH2:17]1)[CH3:19])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 574242534-Bromo-2-cyclopropylaminomethyl-benzoic acid isopropyl ester2회

생성물 1

HCID 574242544-Bromo-2-[(cyclopropyl-methylamino)-methyl]-benzoic acid isopropyl ester수율 88.5%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A solution of 4-bromo-2-cyclopropylaminomethyl-benzoic acid isopropyl ester (Intermediate 119, 1.33 g, 4.26 mmol) in acetone (8 mL) was treated with potassium carbonate (2.36 g, 17.05 mmol) and methyl iodide (0.53 mL, 8.52 mmol) and the resulting reaction mixture was stirred at ambient temperature for 3 h. The volatiles were evaporated in vacuo, the residue was diluted with water and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous magnesium sulfate, filtered over a short bed of silica gel (230–400 mesh) and evaporated in vacuo to afford the title product (1.23 g, 70%).

후처리

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with diethyl ether (×2)
  5. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered over a short bed of silica gel (230–400 mesh)
  7. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-9b267b4302c14901b21133e1bb140f03
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07226951B2

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