Sodium hydride → 7-(3,4-Dimethyl-benzoyl)-5-pyridin-4-ylmethyl-5H-[1,3]dioxolo[4,5-g]quinolin-8-one

HRID 227101

Reaction equation

HRID 227101 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[CH:14]=[C:13]3[O:18][CH2:19][O:20][C:12]3=[CH:11][C:10]=2[NH:9][CH:8]=1)=[O:6].[H-].[Na+].Br.Br[CH2:29][C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[CH:14]=[C:13]3[O:18][CH2:19][O:20][C:12]3=[CH:11][C:10]=2[N:9]([CH2:29][C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 127522194-(Bromomethyl)pyridine hbrHCID 533373387-(3,4-dimethyl-benzoyl)-5H-[1,3]dioxolo[4,5-g]quinolin-8-one

Product 1

HCID 167307717-(3,4-Dimethyl-benzoyl)-5-pyridin-4-ylmethyl-5H-[1,3]dioxolo[4,5-g]quinolin-8-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 71 mg (0.22 mmol) of 7-(3,4-dimethyl-benzoyl)-5H-[1,3]dioxolo[4,5-g]quinolin-8-one, 23 mg of 60% sodium hydride, 72 mg of 4-bromomethylpyridine hydrobromide and 1.3 mL of N,N-dimethylformamide. Yield: 61 mg of a white solid: LC-MSD, m/z for C25H20N2O4 [M+H]+=413.5; HPLC retention time: 1.2 min.

Sources & evidence

ORD record
ord-f7041c322a1a40e8ba3404d141236fdc
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Linked notes

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