3-Bromobenzyl bromide → 1-(3-Bromo-benzyl)-3-(2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one

HRID 227142Notes

Reaction equation

HRID 227142 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][CH:14]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[Br:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]Br)[CH:26]=1>>[Br:24][C:25]1[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=1)[CH2:31][N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22](=[O:23])[C:13]([C:11]([C:9]2[CH:8]=[CH:7][C:6]3[O:1][CH2:2][CH2:3][O:4][C:5]=3[CH:10]=2)=[O:12])=[CH:14]1

Participants

3

Reactant 2

HCID 699793-Bromobenzyl bromideHCID 577545433-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one

Product 1

HCID 577546611-(3-Bromo-benzyl)-3-(2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-oneYield 23%

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one (70 mg, 0.228 mmol) and 74 mg (0.296 mmol) of 1-Bromo-3-bromomethyl-benzene, to give 25 mg of desired compound. LCMS (M+H)+: 476.

Sources & evidence

ORD record
ord-515f84265c1548388c3d3cce7aa311b1
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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