2-bromo-3-trifluoromethylpyridine → HCID 71143997, compound

HRID 2370810Notes

Reaction equation

HRID 2370810 reaction equation
Br[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[I:17][C:18]1[CH:31]=[CH:30][C:21]([CH:22]=[N:23][S:24]([C:26]([CH3:29])([CH3:28])[CH3:27])=[O:25])=[CH:20][CH:19]=1>C1COCC1>[I:17][C:18]1[CH:19]=[CH:20][C:21]([CH:22]([C:2]2[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[NH:23][S:24]([C:26]([CH3:29])([CH3:28])[CH3:27])=[O:25])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 51938202-bromo-3-trifluoromethylpyridineHCID 67981364HCID 67981364, compoundHCID 178418339Butyllithium

Product 1

HCID 71143997HCID 71143997, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-bromo-3-(trifluoromethyl)pyridine (750 mg, 3.32 mmol) (prepared as described in Schlosser, M. et al. Eur. J. Org. Chem. 2003, 1559) in THF (5.0 mL) at −78° C. was added n-butyllithium (3.94 mL, 6.31 mmol, 1.6 M in n-hexane). The resulting mixture was then stirred for 15 min. N-(4-iodobenzylidene)-2-methylpropane-2-sulfinamide (556 mg, 1.66 mmol) in THF (5 mL) was added, and the reaction was allowed to warm to rt and stirred for 4 h. The reaction was quenched with saturated aqueous NH4Cl (10 mL) and stirred rapidly for 1 h. The aqueous layer was extracted with EtOAc (2×10 mL) and the combined organic layers were dried (MgSO4) and concentrated. The product thus obtained was taken into the next step without further purification.

Workup

  1. stirringstirred for 4 h
  2. customThe reaction was quenched with saturated aqueous NH4Cl (10 mL)
  3. stirringstirred rapidly for 1 h
  4. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. customThe product thus obtained
  8. customwas taken into the next step without further purification

Sources & evidence

ORD record
ord-aadf4655742746a887089e45b97bffc6
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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