Hydrochloric Acid → 1-(5-Bromopyridin-3-YL)-2,2,2-trifluoroethan-1-amine

HRID 1253937Notes

Reaction equation

HRID 1253937 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:9]([NH:14]S(C(C)(C)C)=O)[C:10]([F:13])([F:12])[F:11])[CH:6]=[N:7][CH:8]=1>CO>[Br:2][C:3]1[CH:4]=[C:5]([CH:9]([NH2:14])[C:10]([F:11])([F:12])[F:13])[CH:6]=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59578414N-(1-(5-bromopyridin-3-yl)-2,2,2-trifluoroethyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 595784171-(5-Bromopyridin-3-YL)-2,2,2-trifluoroethan-1-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of HCl (4 M in dioxane, 0.557 m, 2.23 mmol) was added to a solution of N-(1-(5-bromopyridin-3-yl)-2,2,2-trifluoroethyl)-2-methylpropane-2-sulfinamide (400 mg, 1.114 mmol) in MeOH (2.5 mL) at room temperature. The resulting mixture was stirred at this temperature for overnight. The solvent was removed in vacuum, and the residue was treated with saturated NaHCO3 solution and extracted with ethyl acetate. The combined extracts were dried over anhydrous Na2SO4. After filtration and concentration, the title compound was obtained (230 mg). ESI-MS m/z: 256.9 [M+1]+; Retention time 1.02 min;

Workup

  1. customThe solvent was removed in vacuum
  2. additionthe residue was treated with saturated NaHCO3 solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  5. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-a57e8454a8b24ada9da3ced687ab1d7c
Source dataset
uspto-grants-2013_06
Patent number
US08455522B2

Reaction notes

Loading…