2-Chloro-5-pyridinesulfonyl chloride → HCID 86630978, compound

HRID 2090701Notes

Reaction equation

HRID 2090701 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=1.[Cl:15][C:16]1[N:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>>[Cl:15][C:16]1[N:21]=[CH:20][C:19]([S:22]([N:12]2[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[CH:9][C:10]([CH:13]=[O:14])=[CH:11]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 469085935-(2-Fluorophenyl)-1H-pyrrole-3-carboxaldehyde

Product 1

HCID 86630978HCID 86630978, compound

Procedure

By a similar reaction as in Reference Example 65 and using 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (893 mg) and 6-chloropyridine-3-sulfonyl chloride (1.30 g), the title compound was obtained as a pale-red solid (yield 1.14 g, 66%). More specifically, 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (893 mg) was dissolved in tetrahydrofuran (10 mL), sodium hydride (60% in oil, 226 mg) was added and the mixture was stirred at room temperature for 15 min. 15-Crown-5 (1.1 mL) was added and the mixture was further stirred at the same temperature for 15 min. 6-Chloropyridine-3-sulfonyl chloride (1.30 g) was added. The reaction mixture was stirred at room temperature for 15 min. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→3:2) to give the title compound as a pale-red solid (yield 1.14 g, 66%).

Workup

  1. customBy a similar reaction as in Reference Example 65

Sources & evidence

ORD record
ord-b91bf592b0c14aba84d5b9f9d8534e12
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

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