Sodium hydride → 8-(3,4-Dimethyl-benzoyl)-6-pyridin-4-ylmethyl-2,3-dihydro-6H-[1,4]dioxino[2,3-g]quinolin-9-one

HRID 227104Notes

Reaction equation

HRID 227104 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[CH:14]=[C:13]3[O:18][CH2:19][CH2:20][O:21][C:12]3=[CH:11][C:10]=2[NH:9][CH:8]=1)=[O:6].[H-].[Na+].Br.Br[CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[CH:14]=[C:13]3[O:18][CH2:19][CH2:20][O:21][C:12]3=[CH:11][C:10]=2[N:9]([CH2:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 127522194-(Bromomethyl)pyridine hbrHCID 577547208-(3,4-dimethyl-benzoyl)-2,3-dihydro-6H-[1,4]dioxino[2,3-g]quinolin-9-one

Product 1

HCID 167306178-(3,4-Dimethyl-benzoyl)-6-pyridin-4-ylmethyl-2,3-dihydro-6H-[1,4]dioxino[2,3-g]quinolin-9-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 58 mg (0.17 mmol) of 8-(3,4-dimethyl-benzoyl)-2,3-dihydro-6H-[1,4]dioxino[2,3-g]quinolin-9-one, 18 mg of 60% sodium hydride, 57 mg of 4-bromomethylpyridine hydrobromide and 1.2 mL of N,N-dimethylformamide. Yield: 52 mg of a white solid: LC-MSD, m/z for C26H22N2O4 [M+H]+=427.5; HPLC retention time: 1.4 min.

Sources & evidence

ORD record
ord-06f9ca2007ec44278e48455768bb220d
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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