Cesium carbonate → 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]acetamide

HRID 2090446

반응식

HRID 2090446 반응식
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.Br[CH2:16][C:17]([NH2:19])=[O:18].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:1][C:2]1([CH3:14])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:13]=[N:12][N:11]([CH2:16][C:17]([NH2:19])=[O:18])[CH:10]=2)[O:3]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

생성물 1

HCID 569657342-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]acetamide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (50 mg, 0.2 mmol), 2-Bromoacetamide (43 mg, 0.31 mmol, Aldrich, Cat. No. 301272), and cesium carbonate (250 mg, 0.77 mmol) in acetonitrile (1 mL) was stirred at 90° C. for 2 h. After cooling it was quenched with water, extracted with ethyl acetate. The extract was washed with water twice, brine once; dried over Na2SO4. After filtration the filtrate was concentrated to yield 45 mg of the product which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=252.1

후처리

  1. temperatureAfter cooling it
  2. customwas quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water twice
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration the filtrate
  7. concentrationwas concentrated

출처 및 근거

ORD 기록
ord-681abdcfcc0648aea47dc9d7db31c577
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436008B2

연결된 노트

불러오는 중…