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

HRID 1831885Notes

Reaction equation

HRID 1831885 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). ES HRMS 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-b6c86bb346244800aa81d038e06bac6b
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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