Ethanesulfonylchloride, 2-chloro- → HCID 66747656, compound

HRID 2035911Notes

Reaction equation

HRID 2035911 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[F:10][C:11]([F:31])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([NH2:24])=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1>C1COCC1>[F:31][C:11]([F:10])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:19]3=[N:24][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:20]3[CH:21]=[CH:22][CH:23]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 66748021HCID 66748021, compound

Product 1

HCID 66747656HCID 66747656, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (60%, 196 mg) in THF (dry) (20 mL) was added 2-chloroethanesulfonyl chloride (0.310 mL) at 0° C. and the mixture was stirred for 10 min at the same temperature. A solution of 3-(4-(difluoro(phenyl)methyl)phenyl)pyridin-2-amine (291 mg) in THF (dry) (10 ml) was added at 0° C. and the mixture was stirred at room temperature under a dry atmosphere with anhydrous calcium chloride tube for 2 hr. The mixture was quenched with water/THF then water at 0° C. and extracted with EtOAc/THF. Silica-gel was added to the organic phase and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (silica gel, eluted with MeOH in EtOAc) and concentrated in vacuo. The residue was washed with IPE to give the title compound (49 mg) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature under a dry atmosphere with anhydrous calcium chloride tube for 2 hr
  2. customThe mixture was quenched with water/THF
  3. extractionwater at 0° C. and extracted with EtOAc/THF
  4. additionSilica-gel was added to the organic phase
  5. customthe volatiles were removed in vacuo
  6. customwas purified by column chromatography (silica gel, eluted with MeOH in EtOAc)
  7. concentrationconcentrated in vacuo
  8. washThe residue was washed with IPE

Sources & evidence

ORD record
ord-978375a972f94857a2561556a8a6eb99
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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