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

HRID 1528563ノート

反応式

HRID 1528563 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-92cc2e91c1e3488a803648c968cfd8f1
出典データセット
uspto-grants-2015_07
特許番号
US09090605B2

反応ノート

読み込み中…