Water → N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2-fluorophenyl]methane sulfonamide

HRID 1591820Notes

Reaction equation

HRID 1591820 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[F:16].[CH3:17][S:18](Cl)(=[O:20])=[O:19].O>N1C=CC=CC=1.C(OCC)(=O)C>[C:14]([C:11]1[N:12]([CH3:13])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:18]([CH3:17])(=[O:20])=[O:19])=[C:3]([F:16])[CH:4]=2)=[CH:9][CH:10]=1)#[N:15]

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 156045005-(4-amino-3-fluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 16051003N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2-fluorophenyl]methane sulfonamideYield 79.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-amino-3-fluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (0.15 g, 0.70 mmol) was dissolved in pyridine (1.5 mL), methane sulfonyl chloride (0.05 mL, 0.63 mmol) was added, the mixture was stirred for 4 hours, and then water was added. The mixture diluted with ethyl acetate and the mixture was washed with water, saturated CuSO4, 2N HCl, brine, dried over MgSO4, and concentrated. Flash chromatography (5%-50% ethyl acetate in hexane) afforded N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2-fluorophenyl]methane sulfonamide (0.147 g).

Workup

  1. washthe mixture was washed with water, saturated CuSO4, 2N HCl, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cfa8ffe108fd4a09bc7211716a478462
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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