Water → HCID 23114635, compound

HRID 2080400Notes

Reaction equation

HRID 2080400 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18]O)=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl.CN(C)C=O.CCCCCC>[N:28]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([CH:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])=[N:13][CH:14]=1)=[N+:29]=[N-:30]

Participants

8

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 230285882-[(4-Chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]-5-(hydroxymethyl)pyridine

Product 1

HCID 23114635HCID 23114635, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 5943Carbon TetrachlorideSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
90 °C

Procedure

The 2-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-5-(hydroxymethyl)pyridine (471 mg, 1.15 mmol) obtained in Example 43 was dissolved in a mixture of carbon tetrachloride (4 ml) and N,N-dimethylformamide (16 ml). To the resulting solution were added sodium azide (112 mg, 1.72 mmol) and triphenylphosphine (451 mg, 1.72 mmol). The resulting mixture was stirred at 90° C. for 3 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed sequentially with water and brine. The resulting organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated under reduced pressure to give the title compound (244 mg, 0.561 mmol, 49%) as a colorless amorphous substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed sequentially with water and brine
  3. dry with materialThe resulting organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. concentrationethyl acetate=3:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4c29f3d11b144d0fa3b37dd1a480933f
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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