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

HRID 2407453Notes

Reaction equation

HRID 2407453 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-7c9917bec46745109c5ec5fbb013bc01
Source dataset
uspto-grants-2014_08
Patent number
US08809545B2

Reaction notes

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