Toluene → 1-(6-bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-6,7-difluoro-1H-quinolin-4-one

HRID 227107Notes

Reaction equation

HRID 227107 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][C:12]([F:19])=[C:13]([F:18])[CH:14]=2)[NH:9][CH:8]=1)=[O:6].[Br:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]Br)[N:26]=1.C1(C)C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1>[Br:24][C:25]1[N:26]=[C:27]([CH2:31][N:9]2[C:10]3[C:15](=[CH:14][C:13]([F:18])=[C:12]([F:19])[CH:11]=3)[C:16](=[O:17])[C:7]([C:5](=[O:6])[C:4]3[CH:20]=[CH:21][C:22]([CH3:23])=[C:2]([CH3:1])[CH:3]=3)=[CH:8]2)[CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 129547962-Bromo-6-(bromomethyl)pyridineHCID 577547893-(3,4-dimethyl-benzoyl)-6,7-difluoro-1H-quinolin-4-one

Product 1

HCID 577547431-(6-bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-6,7-difluoro-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 74 mg (0.24 mmol) of 3-(3,4-dimethyl-benzoyl)-6,7-difluoro-1H-quinolin-4-one, 71 mg (0.28 mmol) of 2-bromo-6-bromomethyl-pyridine, 0.57 mL of 0.5M toluene solution of potassium bis(trimethylsilyl)amide and 2 mL of THF. Yield: 73 mg of a white solid: LC-MSD, m/z for C24H17BrF2N2O2 [M+H]+=483.4, 485.4; HPLC retention time: 2.6 min.

Sources & evidence

ORD record
ord-06249ba5c4e84b3f88f43c99eb24d0de
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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