Methanesulfonyl chloride → N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2-(trifluoromethoxy)phenyl]methanesulfonamide
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]([CH3:18])[C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)=[CH:9][C:8]=1[O:21][C:22]([F:25])([F:24])[F:23]>N1C=CC=CC=1>[C:19]([C:16]1[N:17]([CH3:18])[C:13]([C:10]2[CH:11]=[CH:12][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[C:8]([O:21][C:22]([F:24])([F:25])[F:23])[CH:9]=2)=[CH:14][CH:15]=1)#[N:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Methanesulfonyl chloride (0.05 mL, 0.65 mmol) was added dropwise to a solution of 5-[4-amino-3-(trifluoromethoxy)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile (0.16 g, 0.56 mmol) in dry pyridine (2.0 mL). The solution was heated to 50° C. overnight. The solution was cooled to room temperature and pre-adsorbed onto the Celite™ reagent. The crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 5-30% ethyl acetate in hexane) to afford 0.1 g (50%) of N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2-(trifluoromethoxy)phenyl]methanesulfonamide.
Workup
- temperatureThe solution was cooled to room temperature and pre-adsorbed onto the Celite™ reagent
- customThe crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 5-30% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-fd4cf461d6584a5fb69667c185c7e411
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07291643B2
Reaction notes
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