Dimethylformamide → HCID 86610808, compound

HRID 1444792Notes

Reaction equation

HRID 1444792 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[C:12](=[O:33])[O:13][C:14]2[C:19]([C:20]=1[CH2:21][CH2:22][O:23][CH3:24])=[CH:18][CH:17]=[C:16](OS(C(F)(F)F)(=O)=O)[CH:15]=2.C(OCC)(=O)C.[CH3:40][N:41](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[C:12](=[O:33])[O:13][C:14]2[C:19]([C:20]=1[CH2:21][CH2:22][O:23][CH3:24])=[CH:18][CH:17]=[C:16]([C:40]#[N:41])[CH:15]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11641654HCID 11641654, compound

Product 1

HCID 86610808HCID 86610808, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
150 °C

Procedure

Trifluoro-methanesulfonic acid 3-(2,4-dimethoxy-phenyl)-4-(2-methoxy-ethyl)-2-oxo-2H-chromen-7-yl ester (862 mg, 1.766 mol), Zn (CN)2 (310 mg) and Pd(PPh3)4 (204 mg) were dissolved in DMF (12 mL) at room temperature in a sealed tube. After 10 min, the reaction mixture was heated to 150° C. for 4 h. The reaction mixture was cooled to room temperature and ethyl acetate (200 mL) was added. The reaction mixture was then poured into a separation funnel, washed with water (2×100 ml) and brine (2×100 ml). The organic layer was dried over sodium sulfate and concentrated. The product was purified on silica gel eluted with 30-50% ethyl acetate in hexanes to yield 3-(2,4-Dimethoxy-phenyl)-4-(2-methoxy-ethyl)-2-oxo-2H-chromene-7-carbonitrile as a slightly yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionThe reaction mixture was then poured into a separation funnel
  3. washwashed with water (2×100 ml) and brine (2×100 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product was purified on silica gel
  7. washeluted with 30-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-95fb374fff614a8296429fae723b0b6e
Source dataset
uspto-grants-2010_02
Patent number
US07662975B2

Reaction notes

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