Tetrahydrofuran → HCID 13433423, compound

HRID 971106Notes

Reaction equation

HRID 971106 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](SC(C)C)=[N:6][CH:7]=1.O[O:13][S:14]([O-:16])=O.[K+].C(=O)(O)[O-].[Na+].O1C[CH2:26][CH2:25][CH2:24]1>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:14]([CH:25]([CH3:26])[CH3:24])(=[O:16])=[O:13])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 134334105-Bromo-2-[(1-methylethyl)thio]pyridineHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 13433423HCID 13433423, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-bromo-2-isopropylthiopyridine from Step 1 (2.03 g, 8.75 mmol) in tetrahydrofuran (50 ml) and methanol (25 ml) at 0° C. was added oxone (15.8 g, 25.8 mmol) and then saturated aqueous sodium bicarbonate (25 ml). The resulting mixture was stirred at room temperature for 6 hours. The mixture was quenched with aqueous sodium bicarbonate and partitioned between ethyl acetate and water. The crude product from the organic phase was chromatographed on silica gel eluting with 20% ethyl acetate in hexane to afford the 5-Bromo-2-isopropylsulfonylpyridine compound as a white solid.

Workup

  1. customThe mixture was quenched with aqueous sodium bicarbonate
  2. custompartitioned between ethyl acetate and water
  3. customThe crude product from the organic phase was chromatographed on silica gel eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a437a4651a704ebb8ed4939699b4a305
Source dataset
uspto-grants-2007_12
Patent number
US07312334B2

Reaction notes

Loading…