Potassium Carbonate → HCID 10314231, compound

HRID 1033551Notes

Reaction equation

HRID 1033551 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH:9]3O[CH:8]3[C:7]=2[CH:15]=1)#[N:2].[C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1)#[N:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([C:8]2[C:7]3[CH:15]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=3[O:11][C:10]([CH3:13])([CH3:12])[CH:9]=2)[CH:19]=1)#[N:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2302823-CyanoindoleHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

Product 1

HCID 10314231HCID 10314231, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

The reaction mixture containing 6-cyano-3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-benzopyran (1.5 g, 7.5 mmol) (prepared according to Evans et al., J. Med. Chem., 1983, 26, 1582 and J. Med. Chem., 1986, 29, 2194), 3-cyanoindole (1.46 g, 9.75 mmol) and finely ground potassium carbonate (2.6 g, 18.75 mmol) in dimethylformamide (5.0 mL) was heated at 100° C. for three hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and filtered. The filtrate was washed with water, 1N hydrochloric acid, sodium bicarbonate solution and brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated to yield a colorless solid. This material was purified by flash chromatography (20% ethyl acetate in hexanes) to yield 4-(3-cyano-1H-indol-1-yl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (1.45 g) as a colorless solid, m.p. 192°-193° C. (dichloromethaneisopropyl ether): 1H NMR (CDCl3) δ 7.72 (m, 1 H), 7.6 (s, 1 H), 7.40 (dd, J=8.2 and 1.8 Hz, 1 H), 7.25 (m, 2 H), 7.1 (m, 1 H), 6.90 (d, J=8.7 Hz, 1 H), 6.70 (d, J=2.3 Hz, 1 H), 5.88 (s, 1 H), 1.55 (s, 6 H); 13C NMR (CDCl3) 156.8, 135.6, 135.3, 134.9, 134.4, 129.9, 129.5, 127.3, 126.6, 124.8, 123.0, 120.1, 119.0, 118.2, 114.8, 111.3, 104.5, 88.7, 78.6, 27.9 ppm.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with water, 1N hydrochloric acid, sodium bicarbonate solution and brine
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customto yield a colorless solid
  7. customThis material was purified by flash chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3a1f4a1eaf5f446482251f1c716dc3e8
Source dataset
uspto-grants-1994_05
Patent number
US05310932

Reaction notes

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