3-Hydroxypyridine → HCID 19348004, compound

HRID 1637204Notes

Reaction equation

HRID 1637204 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([S:18]([C:20]2[C:21]3[CH:33]=[CH:32][C:31]([CH2:34]OS(C)(=O)=O)=[CH:30][C:22]=3[S:23][C:24]=2[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:19])[CH:15]=[CH:16][CH:17]=1>CN(C)C=O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([S:18]([C:20]2[C:21]3[CH:33]=[CH:32][C:31]([CH2:34][O:1][C:2]4[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=4)=[CH:30][C:22]=3[S:23][C:24]=2[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:19])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 19347999HCID 19347999, compound

Product 1

HCID 19348004HCID 19348004, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxypyridine (57 mg, 0.6 mmol) was added to a stirred suspension of sodium hydride (24 mg of 60% dispersion in mineral oil, 0.6 mmol) in anhydrous dimethylformamide (2 ml), under a nitrogen atmosphere. After 30 minutes, ethyl 3-[(3-methoxyphenyl)sulfinyl]-6-[(methylsulfonyloxy)methyl]benzo[b]thiophene-2-carboxylate (Preparation 18, 234 mg, 0.5 mmol) was added to the mixture, and the mixture was stirred for 3 hours. The reaction was partitioned between ethyl acetate and water. The organics were separated and washed with water, dried (magnesium sulfate) and evaporated under reduced pressure. The residue was flash chromatographed on silica gel using 2% ethanol in dichloromethane as eluant The semi-pure product was re-chromatographed on silica gel using ethyl acetate, and then crystallised from diethyl ether, to give the title compound as a colourless solid (110 mg).

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. customThe organics were separated
  3. washwashed with water
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated under reduced pressure
  6. customchromatographed on silica gel using 2% ethanol in dichloromethane as eluant The semi-pure product
  7. customwas re-chromatographed on silica gel
  8. customcrystallised from diethyl ether

Sources & evidence

ORD record
ord-f8b74dd0862d4489b7d955be037db8de
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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