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

HRID 1897825Notes

Reaction equation

HRID 1897825 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:13]S(C(C)(C)C)=O)[C:9]([F:12])([F:11])[F:10])[CH:5]=[N:6][CH:7]=1.Cl.O1CCOCC1>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH2:13])[C:9]([F:10])([F:11])[F:12])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 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

To N-(1-(5-bromopyridin-3-yl)-2,2,2-trifluoroethyl)-2-methylpropane-2-sulfinamide (1.5 g, 4.18 mmol) in MeOH (8.35 ml) was added HCl 4N in dioxane (2.088 ml, 8.35 mmol) dropwise, and the mixture stirred at room temperature for 16 h. Concentrated, and then the mixture was quenched with saturated NaHCO3 and extracted with EtOAc two times, dried over magnesium sulfate, filtered, concentrated. The title compound was isolated as a light yellow oil used as is for next step. LC-MS (M+1) 257.0, t=1.05 min

Workup

  1. concentrationConcentrated
  2. customthe mixture was quenched with saturated NaHCO3
  3. extractionextracted with EtOAc two times
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0f7201f8bffd4433a0049795018a45f1
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

Loading…