Bromocyclopentane → 1-Cyclopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 2090450노트

반응식

HRID 2090450 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.[CH:15]1(Br)[CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH:15]1([N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH2:19][CH2:18][CH2:17][CH2:16]1

참가 물질

5

반응물 3

HCID 8728BromocyclopentaneHCID 10796Cesium carbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

생성물 1

HCID 567767301-Cyclopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

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), cyclopentyl bromide (46 mg, 0.31 mmol, Aldrich, Cat. No. C115207), and cesium carbonate (250 mg, 0.77 mmol) in acetonitrile (1 mL) was stirred at 90° C. for 2 hours. After cooling it was quenched with water, extracted with ethyl acetate. The extract was washed with water, brine; dried over Na2SO4. After filtration the filtrate was concentrated to yield 40 mg of the product which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=263.3

후처리

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

출처 및 근거

ORD 기록
ord-e71d4c14de8f4e469f8da2de7dc0f95e
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436008B2

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