Pyridine → N-[3-Bromo-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-4-cyclopropyl-2-methyl-benzamide

HRID 2069828노트

반응식

HRID 2069828 반응식
[Br:1][C:2]1[C:3]([C:9]([CH3:17])([CH3:16])[O:10][SiH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH:24]1([C:27]2[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[C:29]([CH3:36])[CH:28]=2)[CH2:26][CH2:25]1>C1(C)C=CC=CC=1.CCCCCC>[Br:1][C:2]1[C:3]([C:9]([CH3:17])([CH3:16])[O:10][SiH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([NH:8][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][C:27]([CH:24]3[CH2:26][CH2:25]3)=[CH:28][C:29]=2[CH3:36])[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 592165404-Cyclopropyl-2-methylbenzoyl chlorideHCID 178455443HCID 178455443, 화합물

생성물 1

HCID 137328400N-[3-Bromo-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-4-cyclopropyl-2-methyl-benzamide수율 98.7%

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 8058Hexane용매

실험 절차

To a solution of [3-bromo-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenylamine (21.28 g, 67.3 mmol) and anhydrous pyridine (6.5 mL, 80 mmol) in 50 mL of anhydrous toluene was added a solution of 4-cyclopropyl-2-methylbenzoyl chloride (13.25 g, 68.1 mmol) in 50 mL anhydrous toluene dropwise. A precipitate formed immediately upon addition. Stirred the mixture at ambient temperature under nitrogen overnight. Diluted the reaction mixture with 125 mL hexane and filtered off the precipitate. Washed the filtrate with 2×200 mL 1.0 M KHSO4, 2×200 mL 5% NaHCO3, and 250 mL water. Dried the solution over MgSO4 and concentrated in vacuo to obtain N-[3-Bromo-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-4-cyclopropyl-2-methyl-benzamide as a waxy light brown solid (31.54 g, 66.4 mmol). MS (ESI) 474, 476.0 (M+H)+.

후처리

  1. customA precipitate formed immediately upon addition
  2. filtrationfiltered off the precipitate
  3. washWashed the filtrate with 2×200 mL 1.0 M KHSO4, 2×200 mL 5% NaHCO3, and 250 mL water
  4. dry with materialDried the solution over MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-79d012936ea1417c8c9b7cc0ec4e45c9
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299077B2

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