Water → HCID 16051101, compound

HRID 1591829Notes

Reaction equation

HRID 1591829 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.[CH3:20][S:21](Cl)(=[O:23])=[O:22].O>C(Cl)Cl.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:21]([CH3:20])(=[O:23])=[O:22])=[CH:3][C:4]=2[C:16]([F:19])([F:17])[F:18])=[CH:9][CH:10]=1)#[N:15]

Participants

7

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 16050434HCID 16050434, compound

Product 1

HCID 16051101HCID 16051101, compoundYield 70.4%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-[4-amino-2-(trifluoromethyl)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile (0.34 g, 1.3 mmol) was dissolved in CH2Cl2 (5 mL) and pyridine (0.2 mL). Methanesulfonyl chloride (90 μL, 1.2 mmol) was added and the mixture was stirred for 16 hours followed by the addition of water. The mixture was then diluted with ethyl acetate, the mixture was washed with water, 2N HCl, brine, dried over MgSO4, and concentrated. The crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 5-50% ethyl acetate in hexane) to afford 0.29 g of N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-3-(trifluoromethyl)phenyl]-methanesulfonamide.

Workup

  1. washthe mixture was washed with water, 2N HCl, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 5-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8021f9b05b664c0581c0fae9f32e63ab
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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