Sodium Sulfite → {4-[(4-chlorobenzyl)sulfonyl]-1H-pyrrol-2-yl}(2-chloropyridin-3-yl)methanone

HRID 456680Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]([C:10]2[NH:14][CH:13]=[C:12]([S:15](Cl)(=[O:17])=[O:16])[CH:11]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[O-]S([O-])=O.[Na+].[Na+].[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1>O.CC(C)=O>[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][S:15]([C:12]2[CH:11]=[C:10]([C:8]([C:7]3[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=3)=[O:9])[NH:14][CH:13]=2)(=[O:17])=[O:16])=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 60 °C

Procedure

5-[(2-chloropyridin-3-yl)carbonyl]-1H-pyrrole-3-sulfonyl chloride (500 mg, 1.64 mmol), Na2SO3 (413 mg, 3.28 mmol), Na2HPO4 (233 mg, 1.64 mmol) were mixed in 4 mL of water and heated to 60° C. overnight (16 hour). The initial creamy suspension became clear and then cloudy. A solution of 4-chlorobenzyl bromide (337 mg, 1.64 mmol) in acetone (4 mL) was added to the reaction solution dropwise with stirring. The mixture was stirred at 60° C. for 4 hour and then cooled down to room temperature. Quenched with 4 mL of water and stirred for another 1 hour. Filtered and washed with water and acetone to afford the product, {4-[(4-chlorobenzyl)sulfonyl]-1H-pyrrol-2-yl}(2-chloropyridin-3-yl)methanone as white solid 646 mg (90% yield).

Workup

stirringThe mixture was stirred at 60° C. for 4 hour
temperaturecooled down to room temperature
customQuenched with 4 mL of water
stirringstirred for another 1 hour
filtrationFiltered
washwashed with water and acetone

Sources & evidence

ORD record: ord-09e6a116e4b742468c29d31d45b9752f
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186716B2

Reaction notes

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