3-Chloro-2-fluoro-5-hydroxypyridine → 4-[(5-chloro-6-fluoropyridin-3-yl)oxy]-3-cyano-N-(5-fluoropyridin-2-yl)benzenesulfonamide

HRID 2178112Notes

Reaction equation

HRID 2178112 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1F)#[N:2].[Cl:21][C:22]1[C:23]([F:29])=[N:24][CH:25]=[C:26]([OH:28])[CH:27]=1>>[Cl:21][C:22]1[CH:27]=[C:26]([O:28][C:8]2[CH:7]=[CH:6][C:5]([S:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=3)(=[O:12])=[O:11])=[CH:4][C:3]=2[C:1]#[N:2])[CH:25]=[N:24][C:23]=1[F:29]

Participants

3

Reactant 2

HCID 224515553-Chloro-2-fluoro-5-hydroxypyridineHCID 594366003-cyano-4-fluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamide

Product 1

HCID 1176531884-[(5-chloro-6-fluoropyridin-3-yl)oxy]-3-cyano-N-(5-fluoropyridin-2-yl)benzenesulfonamide

Procedure

The title compound was prepared according to the method described for Method Variation 1 using 3-cyano-4-fluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamide (Preparation 2) and 3-chloro-2-fluoro-5-hydroxypyridine and then purified using silica gel column chromatography eluting with 30-35% EtOAc in heptanes.

Workup

  1. custompurified
  2. washeluting with 30-35% EtOAc in heptanes

Sources & evidence

ORD record
ord-5e427315feae431dbc92cb1f7437f91f
Source dataset
uspto-grants-2015_06
Patent number
US09067922B2

Reaction notes

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