Ethanesulfonylchloride, 2-chloro- → HCID 66748462, compound

HRID 1622748Notes

Reaction equation

HRID 1622748 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[Cl:10][C:11]1[CH:30]=[CH:29][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:23]([NH2:28])=[N:24][CH:25]=[CH:26][CH:27]=3)=[CH:18][CH:17]=2)=[CH:13][C:12]=1[O:31][CH3:32]>C1COCC1>[Cl:10][C:11]1[CH:30]=[CH:29][C:14]([O:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[C:23]4=[N:28][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:24]4[CH:25]=[CH:26][CH:27]=3)=[CH:20][CH:21]=2)=[CH:13][C:12]=1[O:31][CH3:32]

Participants

5

Reactant 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 66748309HCID 66748309, compound

Product 1

HCID 66748462HCID 66748462, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (60%, 220 mg) in THF (dry) (20 ml) was added 2-chloroethanesulfonyl chloride (0.347 ml) at 0° C. and the mixture was stirred for 10 min at the same temperature. A solution of 3-(4-(4-chloro-3-methoxyphenoxy)phenyl)pyridin-2-amine (359 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 overnight. 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 and washed with IPE to give the title compound (306 mg) as a white solid. A part of product was recrystallized from MeCN/IPE.

Workup

  1. stirringthe mixture was stirred at room temperature under a dry atmosphere with anhydrous calcium chloride tube overnight
  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. washwashed with IPE

Sources & evidence

ORD record
ord-c90aefa9fcb44218906c736c10e9d4db
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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