HCID 10247482, compound → HCID 9998311, compound

HRID 1453995Notes

Reaction equation

HRID 1453995 reaction equation
[C:1]([C:3]1[CH:12]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)[C:11]2[C:6](=[CH:7][C:8]([O:25][CH3:26])=[CH:9][CH:10]=2)[O:5][CH:4]=1)#[N:2]>CCOC(C)=O>[C:1]([CH:3]1[CH:12]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)[C:11]2[C:6](=[CH:7][C:8]([O:25][CH3:26])=[CH:9][CH:10]=2)[O:5][CH2:4]1)#[N:2]

Participants

3

Reactant 1

HCID 10247482HCID 10247482, compound

Product 1

HCID 9998311HCID 9998311, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Cyano-7-methoxy-4-(3,4,5-trimethoxy-phenyl)-4H-chromene (25 mg, 0.07 mmol) was dissolved into EtOAc (1 mL). The solution was purged with nitrogen, and a catalytic amount of Pd/C 10% was added. The reaction was put under H2 pressure at 60 psi for 5 h. The solution was flushed with nitrogen, filtered on a Celite pad, and the pad was washed with EtOAc (5 mL). The solution was concentrated. Purification with bond elute silica gel using 20% EtOAc/hexane yielded 24 mg (72%) as a white solid. 1H NMR (CDCl3): 6.83 (d, J=8.3 Hz, 1H), 6.51 (d, J=2.6 Hz, 1H), 6.48 (dd, J=2.5, 5.1 Hz, 1H), 6.45 (s, 2H), 4.38-4.33 (m, 3H), 3.86 (s, 3H), 3.80 (s, 9H), 3.40-3.37 (m, 1H).

Workup

  1. customThe solution was purged with nitrogen
  2. additiona catalytic amount of Pd/C 10% was added
  3. customfor 5 h
  4. customThe solution was flushed with nitrogen
  5. filtrationfiltered on a Celite pad
  6. washthe pad was washed with EtOAc (5 mL)
  7. concentrationThe solution was concentrated
  8. customPurification with bond
  9. washelute silica gel using 20% EtOAc/hexane
  10. customyielded 24 mg (72%) as a white solid

Sources & evidence

ORD record
ord-3e81c6b7ab7b43d588aad1d8ac99c006
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

Loading…