Pyridine → HCID 16051100, compound

HRID 1591827Notes

Reaction equation

HRID 1591827 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:13]([CH3:14])[C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)=[C:4]([F:17])[CH:3]=1.[CH:18]([S:21](Cl)(=[O:23])=[O:22])([CH3:20])[CH3:19].N1C=CC=CC=1>O>[C:15]([C:12]1[N:13]([CH3:14])[C:9]([C:5]2[C:4]([F:17])=[CH:3][C:2]([NH:1][S:21]([CH:18]([CH3:20])[CH3:19])(=[O:23])=[O:22])=[C:7]([F:8])[CH:6]=2)=[CH:10][CH:11]=1)#[N:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 824082-Propanesulfonyl chlorideHCID 160504335-(4-Amino-2,5-difluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 16051100HCID 16051100, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

5-(4-amino-2,5-difluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (150 mg, 0.64 mmol) was dissolved in isopropyl sulfonyl chloride (1.0 mL, 9.0 mmol), pyridine (0.2 mL) was added and the mixture was heated to 100° C. for 6 hours. The mixture was then cooled, 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)-2,5-difluorophenyl]propane-2-sulfonamide (26 mg).

Workup

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

Sources & evidence

ORD record
ord-06d1f2f1783d4748bed717e93a6777d4
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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