Tetrahydrofuran → 3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1-(6-methyl-pyridin-2-ylmethyl)-1h-quinolin-4-one

HRID 227073Notes

Reaction equation

HRID 227073 reaction equation
CON(C)[C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=2)[CH:7]=1)=[O:5].[CH2:26]1[CH2:30][O:29][CH2:28][CH2:27]1>C1OC2C(=C[C-]=CC=2)OC1.[Mg+2].[Br-]>[O:5]1[C:4]2[CH:6]=[CH:15][C:14]([C:4]([C:6]3[C:15](=[O:16])[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[N:8]([CH2:17][C:18]4[CH:23]=[CH:22][CH:24]=[C:20]([CH3:21])[N:19]=4)[CH:7]=3)=[O:5])=[CH:27][C:28]=2[O:29][CH2:30][CH2:26]1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 577545121-(6-Methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl amide

Product 1

HCID 577545143-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1-(6-methyl-pyridin-2-ylmethyl)-1h-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 15974803Magnesium bromide 2,3-dihydro-1,4-benzodioxin-6-ide (1/1/1)Solvent

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60, from 161 mg (0.48 mmol) of 1-(6-methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 2.5 mL THF and 2.4 mL 0.5M 3,4-(ethylenedioxy)phenylmagnesium bromide. Yield: 65 mg of a white solid. LC-MSD, m/z for C25H20N2O4 [M+H]+=413.1; HPLC retention time: 1.8 min.

Sources & evidence

ORD record
ord-7fa5f74d6c2b4f34ac57ae07e1582d11
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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