1-Bromo-2-methylpropane → N-isobutyl-N-(5-isopropylpyridin-2-yl)-4-vinylbenzenesulfonamide

HRID 594142

반응식

HRID 594142 반응식
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]=[CH2:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[N:8][CH:9]=1)([CH3:3])[CH3:2].[C:22](N=C(N(C)C)N(C)C)([CH3:25])([CH3:24])[CH3:23].BrCC(C)C>C(#N)C>[CH2:23]([N:10]([C:7]1[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][N:8]=1)[S:11]([C:14]1[CH:15]=[CH:16][C:17]([CH:20]=[CH2:21])=[CH:18][CH:19]=1)(=[O:12])=[O:13])[CH:22]([CH3:25])[CH3:24]

참가 물질

5

반응물 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 89876040N-(5-isopropylpyridin-2-yl)-4-vinylbenzenesulfonamide

생성물 1

HCID 89875813N-isobutyl-N-(5-isopropylpyridin-2-yl)-4-vinylbenzenesulfonamide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of N-(5-isopropylpyridin-2-yl)-4-vinylbenzenesulfonamide (507 mg, 1.677 mmol) in acetonitrile (10 mL), was added 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (0.676 mL, 3.35 mmol). The mixture was stirred at room temperature for 1 hour, then 1-bromo-2-methylpropane (0.676 mL, 3.35 mmol) added. The reaction was then heated by microwaves to 150° C., for 30 minutes. After cooling, the solvent was removed under a stream of nitrogen and the crude purified by normal phase chromatography on silica (Si) (0-50% ethyl acetate-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the title product, 179 mg, as a yellow oil which solidified on standing. LCMS (2 min, High pH) Rt 1.49 min, m/z (ES+) 359 (M+H).

후처리

  1. temperatureThe reaction was then heated by microwaves to 150° C., for 30 minutes
  2. temperatureAfter cooling
  3. customthe solvent was removed under a stream of nitrogen
  4. customthe crude purified by normal phase chromatography on silica (Si) (0-50% ethyl acetate-cyclohexane gradient)
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-b0067cfcdbfa4507a5b4380cd84530c2
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242972B2

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