3-Bromobenzyl bromide → HCID 57754513, compound

HRID 227021Notes

Reaction equation

HRID 227021 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)=[O:9])=[N:6][CH:7]=1.[Br:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Br>CN(C=O)C>[Br:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19](=[O:20])[C:10]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=2)=[O:9])=[CH:11]1

Participants

4

Reactant 2

HCID 699793-Bromobenzyl bromideHCID 57754654HCID 57754654, compound

Product 1

HCID 57754513HCID 57754513, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Experimental conditions analogous to those described for Example 1 step 3 were used with 68 mg (0.257 mmol) of 3-(5-Methyl-pyridine-2-carbonyl)-1H-quinolin-4-one, 77.2 mg (0.309 mmol) of 3-bromobenzyl bromide, 12.4 mg (0.309 mmol, 60% dispersion in oil), and 1 mL of DMF. The crude product was purified by reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA to yield 39.1 mg of 1-(3-Bromo-benzyl)-3-(5-methyl-pyridine-2-carbonyl)-1H-quinolin-4-one as a white solid. LC-MSD, m/z for C23H17BrN2O2 [M+H]: 433.05 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.5 min.

Workup

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

Sources & evidence

ORD record
ord-b8e82067d8a1429283954c883c19dc7b
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

Loading…