Methyl iodide → HCID 58064922, compound

HRID 400714Notes

Reaction equation

HRID 400714 reaction equation
[C:1]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=3)[C:10]([NH:21][C:22]([C:24]3[C:32]4[O:31][CH2:30][O:29][C:28]=4[CH:27]=[CH:26][C:25]=3[Br:33])=[O:23])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[C:40](N)(=O)C1C=CC=CC=1.[H-].[Na+].CI>CN(C=O)C.CCOCC>[C:1]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:2]=[CH:3][C:4]([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=3)[C:10]([N:21]([CH3:40])[C:22]([C:24]3[C:32]4[O:31][CH2:30][O:29][C:28]=4[CH:27]=[CH:26][C:25]=3[Br:33])=[O:23])=[CH:9][CH:8]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66681528HCID 66681528, compound

Product 1

HCID 58064922HCID 58064922, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of benzamide N-(4-(biphenyl-4-yl)-6,7-dimethoxynaphthalen-1-yl)5-bromobenzo[1,3]dioxole-4-carboxamide (1 mmol), and NaH (3 mmol) in dry DMF (20 mL) was added MeI (2 equiv). The reaction mixture was stirred over night, diluted with ether and then washed with 10% HCl and brine. The residue was subjected to column chromatography on silica using 2% methanol in chloroform to provide product N-(4-(biphenyl-4-yl)-6,7-dimethoxynaphthalen-1-yl)5-bromo-N-methylbenzo[1,3]dioxole-4-carboxamide as an off white solid. 1H NMR (400 MHz) (CDCl3) δ 3.39-3.60 (m, 3H, N—CH3), 3.66-3.80 (m, 3H, O—CH3), 3.96-4.00 (m, 3H, O—CH3), 5.03-6.18 (m, 2H, O—CH2O), 6.30-7.69 (m, 15H, aromatic).

Workup

  1. washwashed with 10% HCl and brine

Sources & evidence

ORD record
ord-606aeaf5452c42b38e5450389fb256e4
Source dataset
uspto-grants-2014_06
Patent number
US08741917B2

Reaction notes

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