Potassium Carbonate → HCID 10573224, compound

HRID 862482Notes

Reaction equation

HRID 862482 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH2:15][O:16][CH3:17])([CH2:12][O:13][CH3:14])[CH:9]3[O:18][CH:8]3[C:7]=2[CH:19]=1)#[N:2].[C:20]([C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)#[N:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH2:15][O:16][CH3:17])([CH2:12][O:13][CH3:14])[C@@H:9]([OH:18])[C@H:8]([N:24]3[C:25]4[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:22]([C:20]#[N:21])=[CH:23]3)[C:7]=2[CH:19]=1)#[N:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2302823-CyanoindoleHCID 19698431HCID 19698431, compound

Product 1

HCID 10573224HCID 10573224, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture containing 6-cyano-3,4-epoxy-3,4-dihydro-2,2-bis(methoxymethyl)-2H-1-benzopyran (300 mg), 3-cyanoindole (210 mg) and potassium carbonate (480 mg), in dimethylformamide (3 ml), was stirred at 80° C. for 2.5 hours. The reaction mixture was diluted with ethyl acetate, washed with water, 1N-hydrochloric acid, an aqueous solution of sodium hydrogencarbonate and brine, dried over anhydrous sodium sulfate and concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) to give 298 mg of the title compound.

Workup

  1. washwashed with water, 1N-hydrochloric acid
  2. dry with materialan aqueous solution of sodium hydrogencarbonate and brine, dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-7975a37015554bde832f5dd5c2223ca7
Source dataset
uspto-grants-1998_02
Patent number
US05719155

Reaction notes

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