Ammonia → 1-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one

HRID 2202899Notes

Reaction equation

[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:18]1[CH:19]=[CH:20][C:21]2[N:25]=[C:24]([CH2:26][CH3:27])[N:23]([CH3:28])[C:22]=2[CH:29]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC.N>[Cu](I)I.CS(C)=O>[CH2:26]([C:24]1[N:23]([CH3:28])[C:22]2[CH:29]=[C:18]([N:11]3[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]4[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=4)=[CH:9][C:10]3=[O:14])[CH:19]=[CH:20][C:21]=2[N:25]=1)[CH3:27]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (5 g), 6-bromo-2-ethyl-1-methyl-1H-benzimidazole (6.54 g), potassium carbonate (9.46 g), N,N′-dimethylethylenediamine (2.91 ml), copper iodide (1.3 g) and DMSO (100 ml) was stirred at 150° C. for 4 h. After cooling, the mixture was poured into 28% NH3 solution at 0° C. The precipitate was collected by filtration and dissolved in EtOAc/THF. The resulting solution was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was treated with activated carbon in MeOH, and recrystallized from MeOH/water to give the title compound (3.44 g) as a white solid.

Workup

temperatureAfter cooling
filtrationThe precipitate was collected by filtration
dissolutiondissolved in EtOAc/THF
washThe resulting solution was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
additionThe residue was treated with activated carbon in MeOH
customrecrystallized from MeOH/water

Sources & evidence

ORD record: ord-d341405b80b94f5183d5601df1004d0e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

Loading…