Potassium Carbonate → HCID 68517072, compound

HRID 1716293Notes

Reaction equation

HRID 1716293 reaction equation
Cl[CH2:2][C:3]1[C:4]([O:9][CH3:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[C:11]1([CH3:29])[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.O>[CH3:10][O:9][C:4]1[C:3]([CH2:2][N:24]([C:21]2[CH:20]=[CH:19][C:18]([O:17][C:14]3[CH:15]=[CH:16][C:11]([CH3:29])=[CH:12][CH:13]=3)=[CH:23][CH:22]=2)[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3858049N-[4-(4-methylphenoxy)phenyl]methanesulfonamideHCID 149329453-(Chloromethyl)-2-methoxypyridine

Product 1

HCID 68517072HCID 68517072, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-chloromethyl-2-methoxy-pyridine (0.2 g, 1.29 mmol) from Step A, N-(4-p-tolyloxy-phenyl)-methanesulfonamide (0.38 g, 1.35 mmol) from Step B and K2CO3 (0.44 g, 3.22 mmol) in dry DMF (5 mL) was heated at 70° C. overnight. The reaction was then diluted with EtOAc/H2O. The aqueous layer was extracted with EtOAc (×2) and the combined organics were brought to the usual work-up. The resulting crude material was purified by chromatography (silica gel, 40% EtOAc/hexanes) to give the desired product. MS (EI) 399 (M+H)+.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (×2)
  2. customThe resulting crude material was purified by chromatography (silica gel, 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6d1fa34900c049bd8a1b9c06b75c8500
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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