Water → HCID 21107099, compound

HRID 1765397Notes

Reaction equation

HRID 1765397 reaction equation
Br[C:2]1[C:7]2[C:8](=[O:20])[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:10][O:11][C:6]=2[CH:5]=[C:4]([O:21][CH3:22])[CH:3]=1.[Cu][C:24]#[N:25].O>CN(C=O)C>[C:24]([C:2]1[C:7]2[C:8](=[O:20])[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:10][O:11][C:6]=2[CH:5]=[C:4]([O:21][CH3:22])[CH:3]=1)#[N:25]

Participants

5

Reactant 3

HCID 962WaterHCID 21107090HCID 21107090, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 21107099HCID 21107099, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 5-bromo-7-methoxy-3-(4-methoxyphenyl)-4-oxo-4H-1 benzopyran (150 mg), copper(I) cyanide (55.5 mg) in DMF (4 mL) was heated at 120° C. for 3 h. The mixture was cooled, poured into cold water and extracted with ethyl acetate. The organic layer was washed with 1M hydrochloric acid, saturated aqueous sodium bicarbonate and brine, and dried over MgSO4. Evaporation of the solvents afforded the title compound (126 mg) as a white solid. 1H NMR (DMSO-d6): 8.52 (s, 1H), 7.67 (d, 1H, J=2.7 Hz), 7.54 (m, 3H), 7.01 (d, 2H, J=8.7 Hz), 3.97 (s, 3H), 3.80 (s, 3H); MS: 308 (MH+); HPLC tR: 2.29 min.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 1M hydrochloric acid, saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvents

Sources & evidence

ORD record
ord-159ec9388eb74f5ab8880cc5f5c450ba
Source dataset
uspto-grants-2007_06
Patent number
US07226945B2

Reaction notes

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