Potassium Carbonate → HCID 69029207, compound

HRID 1868613Notes

Reaction equation

HRID 1868613 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10]([OH:17])[CH:9]=2.Br[C:24]([Br:27])([CH3:26])C.[C:28](=O)([O-])[O-].[K+].[K+].[K+].[Br-]>CN(C)C=O>[Br:27][CH2:24][CH2:26][CH2:28][O:17][C:10]1[CH:9]=[C:8]2[C:13]([C:14](=[O:16])[CH:15]=[C:6]([C:5]3[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:3]([O:2][CH3:1])[CH:4]=3)[O:7]2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 116582,2-DibromopropaneHCID 253877Potassium BromideHCID 53785182-(3,4-Dimethoxyphenyl)-7-hydroxy-4H-chromen-4-one2×

Product 1

HCID 69029207HCID 69029207, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound (61) was prepared from 3′,4′-dimethoxy-7-hydroxy-flavone, 27 (3 g, 10 mmol), dibromo propane (4 mL, 39.2 mmol) and potassium carbonate (2.8 g, 20 mmol) in dry dimethyl formamide (150 mL) using the identical procedure as described for 56. Yield 3.4 g (80%); mp 148-149° C.; MS (FAB) 419/421 (M++1); IR (KBr) 1630; 1H NMR (200 MHz, CDCl3) δ 8.12 (d, J=9.5 Hz, 1H), 7.53 (dd, J=8.5 Hz, 2.0 Hz, 1H), 7.36 (d, J=1.9 Hz, 1H), 6.99-6.95 (m, 3H), 6.68 (s, 1H), 4.24 (t, J=5.8 Hz, 2H), 3.98 (s, 3H), 3.96 (s, 3H), 3.64 (t, J=6.3 Hz, 2H), 2.39 (q, J=6.1 Hz, 2H).

Sources & evidence

ORD record
ord-ad00632e1f604c52987b8464b6586244
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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