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

HRID 1591821Notes

Reaction equation

HRID 1591821 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].[CH2:17]([S:19](Cl)(=[O:21])=[O:20])[CH3:18].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:19]([CH2:17][CH3:18])(=[O:21])=[O:20])=[C:3]([F:16])[CH:4]=2)=[CH:9][CH:10]=1)#[N:15]

Participants

6

Reactant 3

HCID 962WaterHCID 11667Ethanesulfonyl chlorideHCID 156045005-(4-amino-3-fluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 16051004N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2-fluorophenyl]ethane sulfonamideYield 31.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-amino-3-fluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (0.31 g, 1.44 mmol) was dissolved in pyridine (3 mL), ethane sulfonyl chloride (0.12 mL, 1.3 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]ethane sulfonamide (0.127 g). HPLC purity 100% at 210-370 nm, 8.3 min.; the Xterra™ RP18 instrument, 3.5/, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (Ammon. Form. Buff. Ph=3.5/ACN+MeOH) for 10 min., hold 4 min. HRMS: calcd for C14H14FN3O2S+H+, 308.08635; found (ESI, [M+H]+), 308.0855.

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-0865442f45f44297aedc078fa717964f
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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