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

HRID 391341Notes

Reaction equation

HRID 391341 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-5dbc2d30297341b7ac2f39bdfb3263af
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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