Tetrahydrofuran → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one

HRID 227037Notes

Reaction equation

HRID 227037 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]([Br: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-]>[Br:24][C:20]1[N:19]=[C:18]([CH2:17][N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15](=[O:16])[C:6]([C:4]([C:15]3[CH:14]=[CH:27][C:28]4[O:29][CH2:30][CH2:26][O:5][C:4]=4[CH:6]=3)=[O:5])=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 577545321-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide

Product 1

HCID 577545961-(6-Bromo-pyridin-2-ylmethyl)-3-(2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-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 90 mg (0.22 mmol) of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 1 mL THF and 0.98 mL 0.5M 3,4-(ethylenedioxy)phenylmagnesium bromide. Yield: 77 mg of a white solid. LC-MSD, m/z for C24H17BrN2O4 [M+H]+=477.0, 479.0; HPLC retention time: 2.4 min.

Sources & evidence

ORD record
ord-2b391626fefb4e13b383956861fe4c57
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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