Hydrochloric Acid → 6-Bromo-α-(trifluoromethyl)-3-pyridinemethanamine

HRID 559778Notes

Reaction equation

HRID 559778 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([NH:13]S(C(C)(C)C)=O)[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.Cl.O1CCOCC1>CO.C(=O)([O-])[O-].[K+].[K+]>[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([NH2:13])[C:9]([F:10])([F:11])[F:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59278354HCID 59278354, compound

Product 1

HCID 592785116-Bromo-α-(trifluoromethyl)-3-pyridinemethanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a solution of 2-methyl-propane-2-sulfinic acid [1-(6-bromo-pyridin-3-yl)-2,2,2-trifluoro-ethyl]-amide (1.17 g, 3.26 mmol) in methanol (15 mL) was added a 4 N solution of HCl in dioxane (2 mL, 8.0 mmol). The reaction was monitored by TLC (ethyl acetate-hexanes 3:7). The mixture was diluted with saturated aqueous potassium carbonate and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine (3×15 mL), dried over magnesium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography eluting with ethyl acetate-hexanes (1:9, then 2:8) to afford the title compound as a clear oil.

Workup

  1. extractionextracted with ethyl acetate (3×25 mL)
  2. washThe combined organic layers were washed with brine (3×15 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with ethyl acetate-hexanes (1:9

Sources & evidence

ORD record
ord-8ba262a773e145c6a63991c70d2c9140
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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