Potassium Carbonate → HCID 69030155, compound

HRID 1868612Notes

Reaction equation

HRID 1868612 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1)[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:4]=[C:3]([O:2][CH3:1])[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=3)[O:7]2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 116582,2-DibromopropaneHCID 253877Potassium BromideHCID 69030367HCID 69030367, compound2×

Product 1

HCID 69030155HCID 69030155, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound (60) was prepared from 3′,5′-dimethoxy-7-hydroxy-flavone, 26 (1.1 g, 3.7 mmol), dibromo propane (1.9 mL, 18.5 mmol) and potassium carbonate (1.5 g, 11.1 mmol) in dry dimethyl formamide (100 mL) using the identical procedure as described for 56. Yield 1.1 g (74%); mp 173-174° C.; MS (FAB) 419/421 (M++1); IR (KBr) 1631; 1H NMR (200 MHz, DMSO-d6) δ 7.88 (d, J=8.8 Hz, 1H), 7.35 (d, J=2.1 Hz, 1H), 7.17 (d, J=2.1 Hz, 2H), 7.02 (dd, J=8.9 Hz, 2.2 Hz, 1H), 6.98 (s, 1H), 6.66 (s, 1H), 4.19 (t, J=5.9 Hz, 2H), 3.79 (s, 6H), 3.64 (t, J=6.4 Hz, 2H), 2.26 (q, J=6.2 Hz, 2H).

Sources & evidence

ORD record
ord-3656ff27fe7848bc9b63cdbe42683555
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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