Water → HCID 23114635, compound

HRID 748843Notes

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.C(OCC)(=O)C.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

Conditions

Temperature: 90 °C

Procedure

In a mixture of carbon tetrachloride (4 ml) and N,N-dimethylformamide (16 ml) was dissolved the 2-[(4-chlorophenylsulfonyl) (2,5-difluorophenyl)methyl]-5-(hydroxymethyl)pyridine (471 mg, 1.15 mmol) obtained in Example 331. Sodium azide (112 mg, 1.72 mmol) and triphenylphosphine (451 mg, 1.72 mmol) were added and the 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 then washed successively with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to chromatography on a silica gel column. A fraction obtained from the elution portion with hexane:ethyl acetate=3:1 was concentrated under reduced pressure, whereby the title compound (244 mg, 0.561 mmol, 49%) was obtained as a colorless amorphous substance.

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was then washed successively with water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue thus obtained

Sources & evidence

ORD record: ord-6836e3ba3df342e8bea4f002f9d7ddd4
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399775B2

Reaction notes

Loading…