Pyridine → HCID 16051186, compound

HRID 1591830Notes

Reaction equation

HRID 1591830 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)=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1.[CH:20]([S:23](Cl)(=[O:25])=[O:24])([CH3:22])[CH3:21].N1C=CC=CC=1>O>[C:14]([C:11]1[N:12]([CH3:13])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:23]([CH:20]([CH3:22])[CH3:21])(=[O:25])=[O:24])=[CH:3][C:4]=2[C:16]([F:19])([F:17])[F:18])=[CH:9][CH:10]=1)#[N:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 824082-Propanesulfonyl chlorideHCID 16050434HCID 16050434, compound

Product 1

HCID 16051186HCID 16051186, compoundYield 10.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

5-[4-amino-2-(trifluoromethyl)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile (0.33 g, 1.25 mmol) was dissolved in isopropyl sulfonyl chloride (1.0 mL, 9.0 mmol), pyridine (0.5 mL) was added, and the mixture was heated to 100° C. for 6 hours. The mixture was cooled and diluted with water and extracted with ethyl acetate. The organics were combined, washed with water, brine, dried over MgSO4, and concentrated. Flash chromatography (0%-100% ethyl acetate in hexane) afforded N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-3-(trifluoromethyl)phenyl]-propane-2-sulfonamide (50 mg).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8b4431de21bd471aa181136058914ac3
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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