Water → HCID 70275202, compound

HRID 1416966Notes

Reaction equation

HRID 1416966 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[N:3]=1.[O-:27][CH2:28][CH3:29].[Na+].O>C(O)C>[CH2:28]([O:27][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[N:3]=1)[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 53669110HCID 53669110, compound

Product 1

HCID 70275202HCID 70275202, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

2-Chloro-6-(4-fluorophenyl-5-[4-(methylsulfonyl)phenyl]pyridine-3-carbonitrile (Example 7) (200 mg, 0.52 mMol) was added to freshly prepared sodium ethoxide (0.57 mMol) (from addition of sodium metal to ethyl alcohol) in ethyl alcohol (50 ml) and heated to 65° C. for 3.5 hours. The reaction mixture was cooled to room temperature. Water (3 ml) was added and the mixture was concentrated. The product was partitioned between water (50 ml) and ethyl acetate (50 ml). The ethyl acetate portion was dried over sodium sulfate, filtered and concentrated to a solid. The product was purified by a silica gel chromatography to give a white solid: m.p. (DSC): 207.22° C. Anal. Calc'd. for C21H17N2O3SF (396.44): C, 63.62; H, 4.32; N, 7.07. Found: C, 63.56; H, 4.32; N, 6.88.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationthe mixture was concentrated
  3. customThe product was partitioned between water (50 ml) and ethyl acetate (50 ml)
  4. dry with materialThe ethyl acetate portion was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a solid
  7. customThe product was purified by a silica gel chromatography
  8. customto give a white solid

Sources & evidence

ORD record
ord-7936a1a0e9c84b2f98108a7e0771f1e1
Source dataset
uspto-grants-1999_06
Patent number
US05916905

Reaction notes

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