Methanesulfonyl chloride → N-(3-fluoro-4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]phenyl}-methanesulfonamide

HRID 369403Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[N:11]([CH3:24])[C:12]([C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:13]([CH3:15])[CH:14]=1)[NH2:5].[CH3:25][S:26](Cl)(=[O:28])=[O:27]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:5][S:26]([CH3:25])(=[O:28])=[O:27])[CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[N:11]([CH3:24])[C:12]([C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:13]([CH3:15])[CH:14]=1

Participants

Conditions

Temperature: -5 °C

Procedure

3-Fluoro-4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]aniline (1.0 g, 3.1 mmol) [prepared as described in Example 1] was dissolved in pyridine (10 ml) and the solution was cooled to -5° C. Methanesulfonyl chloride (0.39 g, 3.4 mmol) was added and after 1 h the reaction mixture was poured into 1M HCl/ice/water and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated to dryness. The residue was crystallized from methylene chloride-methanol to give N-{3-fluoro-4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]phenyl}-methanesulfonamide (775 mg, 62%) as a solid, mp 165-167° C.

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated to dryness
customThe residue was crystallized from methylene chloride-methanol

Sources & evidence

ORD record: ord-12b0678d601d49a7bde8ad5123f38611
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136844

Reaction notes

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