Hydrochloric Acid → 1-Benzyl-6-methyl-2-oxo-1,2-dihydropyridin-4-yl 4-bromobenzenesulfonate

HRID 1866870Notes

Reaction equation

HRID 1866870 reaction equation
[CH2:1]([N:8]1[C:13]([CH3:14])=[CH:12][C:11]([OH:15])=[CH:10][C:9]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.Cl>[Cl-].[Na+].O.CN(C=O)C>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O:15][C:11]2[CH:12]=[C:13]([CH3:14])[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:9](=[O:16])[CH:10]=2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7396p-Bromobenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 54678659HCID 54678659, compound

Product 1

HCID 865915871-Benzyl-6-methyl-2-oxo-1,2-dihydropyridin-4-yl 4-bromobenzenesulfonate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

1-benzyl-4-hydroxy-6-methylpyridin-2(1H)-one (from example 35) (10 mmol, 2.15 g), N,N′-dimethylformamide (30 mL), potassium carbonate (20 mmol, 2.76 g), and 4-bromobenzenesulfonyl chloride (10 mmol, 2.55 g) were stirred at room temperature for 16 hours. Hydrochloric acid (1N) was added until the mixture was acidic to pH paper. Brine (50 mL) was added and the mixture extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine and dried over magnesium sulfate, and filtered. After concentrating, the material was purified by flash column chromatography eluting with ethyl acetate:hexanes (1:2). The appropriate fractions were concentrated to a clear oil, which solidified upon standing several days to a white solid. (3.3 g, 76%): 1H NMR (DMSO-d6/400 MHz) 7.9 (m, 4H), 7.32-7.00 (m, 5H), 7.3 (m, 1H), 6.12 (d, J=2.4 Hz, 1H), 6.02 (d, J=2.8 Hz, 1H), 5.20 (s, 2H), 2.2 (s, 3H). ESHRMS m/z 436.002 (M+H, C19H16NO4SBr requires 436.004).

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×50 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationAfter concentrating
  6. customthe material was purified by flash column chromatography
  7. washeluting with ethyl acetate:hexanes (1:2)
  8. concentrationThe appropriate fractions were concentrated to a clear oil, which
  9. waitupon standing several days to a white solid

Sources & evidence

ORD record
ord-9d524ef52a7341d6aad660e9b4ac9699
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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