Ammonium Chloride → 1-(5-Bromopyridin-2-yl)cyclopropane-1-carbonitrile

HRID 1528563노트

반응식

HRID 1528563 반응식
C[Si](C)(C)[N-][Si](C)(C)C.[K+].[Br:11][C:12]1[CH:13]=[CH:14][C:15](F)=[N:16][CH:17]=1.[CH:19]1([C:22]#[N:23])[CH2:21][CH2:20]1.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([C:19]2([C:22]#[N:23])[CH2:21][CH2:20]2)=[N:16][CH:17]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 79637CyclopropanecarbonitrileHCID 27831685-Bromo-2-fluoropyridineHCID 3251421Potassium bis(trimethylsilyl)amide

생성물 1

HCID 534029901-(5-Bromopyridin-2-yl)cyclopropane-1-carbonitrile

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Potassium hexamethyldisilazide (0.5 mol/L in toluene, 34 mL) was added over a period of 5 min to a solution of 5-bromo-2-fluoro-pyridine (1.50 g) and cyclopropanecarbonitrile (0.63 mL) in toluene (2 mL) chilled in an ice bath. Aqueous NH4Cl solution was then added and the resulting mixture was extracted with ethyl acetate. The combined extracts were dried (Na2SO4) and the solvent was evaporated. The residue was chromatographed on silica gel (cyclohexane/ethyl acetate 1:0→8:2) to give the title compound as a colorless solid. Yield: 0.19 g (10% of theory); LC (method 2): tR=3.34 min; Mass spectrum (ESI+): m/z=223/225 (Br) [M+H]+.

후처리

  1. temperaturechilled in an ice bath
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customthe solvent was evaporated
  5. customThe residue was chromatographed on silica gel (cyclohexane/ethyl acetate 1:0→8:2)

출처 및 근거

ORD 기록
ord-92cc2e91c1e3488a803648c968cfd8f1
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090605B2

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