2-Propanethiol → 5-Bromo-2-[(1-methylethyl)thio]pyridine

HRID 971105Notes

Reaction equation

HRID 971105 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][CH:10]([SH:12])[CH3:11].[H-].[Na+]>CN(C)C=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([S:12][CH:10]([CH3:11])[CH3:9])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

Product 1

HCID 134334105-Bromo-2-[(1-methylethyl)thio]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2,5-dibromopyridine (2.07 g, 8.73 mmol) and 2-propanethiol (0.97 ml, 10.4 mmol) in N,N-dimethylformamide (20 ml) at 0° C. was added portionwise sodium hydride 60% dispersed in oil (450 mg, 11.3 mmol). The resulting mixture was stirred at room temperature for 1 hour, then partitioned between ether and water. The crude product from the organic phase was chromatographed on silica gel eluting with 10% ethyl acetate in hexane to afford the 5-Bromo-2-isopropylthiopyridine compound as a solid.

Workup

  1. custompartitioned between ether and water
  2. customThe crude product from the organic phase was chromatographed on silica gel eluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0acf566bc57c49e9ab6a97582f24db6f
Source dataset
uspto-grants-2007_12
Patent number
US07312334B2

Reaction notes

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