Methanesulfonyl chloride → N-[3-fluoro-4-(4-fluorophenyl)-2,2-dimethyl-2H-chromen-7-yl]methanesulfonamide

HRID 1959109Notes

Reaction equation

HRID 1959109 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[C:8]([CH3:26])([CH3:25])[O:9][C:10]2[C:15]([C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)=[CH:14][CH:13]=[C:12]([NH2:24])[CH:11]=2>N1C=CC=CC=1>[F:6][C:7]1[C:8]([CH3:26])([CH3:25])[O:9][C:10]2[C:15]([C:16]=1[C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)=[CH:14][CH:13]=[C:12]([NH:24][S:2]([CH3:1])(=[O:4])=[O:3])[CH:11]=2

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59442934HCID 59442934, compound

Product 1

HCID 25183423N-[3-fluoro-4-(4-fluorophenyl)-2,2-dimethyl-2H-chromen-7-yl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Under ice-cooling, pyridine (4 mL) and Methanesulfonyl chloride (60 μL) were added dropwise to a solution of [3-fluoro-4-(4-fluorophenyl)-2,2-dimethyl-2H-chromen-7-yl]amine (a compound of Reference Example 7(7), 105 mg) in pyridine (4 mL) and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated in vacuo, the residue was diluted with ethyl acetate, and the solution was washed successively with a saturated aqueous solution of citric acid, water, a saturated aqueous solution of sodium bicarbonate and brine. The organic layer was filtered through a column of porous diatomite (Chem Elut), and the filtrate was concentrated in vacuo. The resultant residue was purified by column chromatography on NH-silica gel (Chromatorex NH-silica gel, Solvent: chloroform/methanol=100/0 to 90/10) to give the titled compound (105 mg) as a colorless powder.

Workup

  1. temperatureUnder ice-cooling
  2. concentrationThe reaction solution was concentrated in vacuo
  3. additionthe residue was diluted with ethyl acetate
  4. washthe solution was washed successively with a saturated aqueous solution of citric acid, water
  5. filtrationThe organic layer was filtered through a column of porous diatomite (Chem Elut)
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resultant residue was purified by column chromatography on NH-silica gel (Chromatorex NH-silica gel, Solvent: chloroform/methanol=100/0 to 90/10)

Sources & evidence

ORD record
ord-137c2c026d504c38ad2e57846f907b83
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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