Dimethylamine → 3-bromo-4-(2,4-difluorobenzyloxy)-1-(4-dimethylaminomethylbenzyl)-1H-pyridin-2-one

HRID 1866900Notes

Reaction equation

HRID 1866900 reaction equation
[Br:1][C:2]1[C:3](=[O:27])[N:4]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25]Cl)=[CH:21][CH:20]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].[CH3:28][NH:29][CH3:30]>C1COCC1>[Br:1][C:2]1[C:3](=[O:27])[N:4]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][N:29]([CH3:30])[CH3:28])=[CH:21][CH:20]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 220500273-bromo-1-(4-chloromethylbenzyl)-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one

Product 1

HCID 113857123-bromo-4-(2,4-difluorobenzyloxy)-1-(4-dimethylaminomethylbenzyl)-1H-pyridin-2-oneYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a sealed tube containing 3-bromo-1-(4-chloromethylbenzyl)-4-(2,4-difluoro-benzyloxy)-1H-pyridin-2-one (0.49 g, 1.1 mmol) was added a solution of dimethylamine (5.5 mL of a 2.0 M solution in THF, 11 mmol), and the reaction mixture was stirred for 15 h. The solvent was removed under reduced pressure. Purification by flash column chromatography (silica, eluent methylene chloride to 92:7.2:0.8 methylene chloride/methanol/ammonia) provided 3-bromo-4-(2,4-difluorobenzyloxy)-1-(4-dimethylaminomethylbenzyl)-1H-pyridin-2-one as a light yellow solid (0.23 g, 46%): mp 111-113° C.; 1H NMR (500 MHz, CDCl3) δ 7.50-7.49 (m, 1H), 7.26-7.22 (m, 5H), 6.90-6.88 (m, 1H), 6.82-6.78 (m, 1H), 6.04 (d, J=6 Hz, 1H), 5.16 (s, 2H), 5.11 (s, 2H), 3.37 (s, 2H), 2.19 (s, 6H). ESHRMS m/z 463.0782 (M+H C22H22BrF2N2O2 requires 463.0827)

Workup

  1. customThe solvent was removed under reduced pressure
  2. customPurification by flash column chromatography (silica, eluent methylene chloride to 92:7.2:0.8 methylene chloride/methanol/ammonia)

Sources & evidence

ORD record
ord-9a0b0d5541254a36b2faa3e7823258e0
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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