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

HRID 1831916Notes

Reaction equation

HRID 1831916 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). ES HRMS 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-1da5d8535219424b85e7a29a96b8b18b
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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