3-Bromobenzyl bromide → 1-(3-Bromo-benzyl)-3-(3-fluoro-4-methoxy-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one

HRID 227017Notes

Reaction equation

HRID 227017 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:18])[N:14]=2)[NH:9][CH:8]=1)=[O:6].[Br:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Br>CN(C)C=O>[Br:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][N:9]1[C:10]2[C:15](=[N:14][C:13]([CH3:18])=[CH:12][CH:11]=2)[C:16](=[O:17])[C:7]([C:5](=[O:6])[C:4]2[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:2]([F:1])[CH:3]=2)=[CH:8]1

Participants

4

Reactant 2

HCID 699793-Bromobenzyl bromideHCID 577546273-(3-Fluoro-4-methoxy-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one

Product 1

HCID 577547481-(3-Bromo-benzyl)-3-(3-fluoro-4-methoxy-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-oneYield 38.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1 were used with 112 mg (0.358 mmol) of 3-(3-Fluoro-4-methoxy-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one, 107.5 mg (0.430 mmol) of 3-bromobenzyl bromide, 17.2 mg (0.430 mmol, 60% dispersion in oil), and 2 mL of N,N-dimethylformamide. The crude product was purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA to yield 67 mg of 1-(3-Bromo-benzyl)-3-(3-fluoro-4-methoxy-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one. LC-MSD, m/z for C24H18BrFN2O3 [M+H]: 481.05. LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.7 min

Workup

  1. customThe crude product was purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA

Sources & evidence

ORD record
ord-5d4f205048ed456a8192a619520f6fb6
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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