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

HRID 1528563Notes

Reaction equation

HRID 1528563 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-92cc2e91c1e3488a803648c968cfd8f1
Source dataset
uspto-grants-2015_07
Patent number
US09090605B2

Reaction notes

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