Water → 5-[4-(4-[1,2,3]Triazol-1-yl-butyl)-phenoxymethyl]-[2-(4-trifluoromethyl-phenyl)]-pyridine

HRID 33482Notes

Reaction equation

[H-].[Na+].[N:3]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH:7]=[CH:6][N:5]=[N:4]1.Cl[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)=[N:25][CH:26]=1.O>CN(C)C=O>[N:3]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]4[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=4)=[N:25][CH:26]=3)=[CH:16][CH:17]=2)[CH:7]=[CH:6][N:5]=[N:4]1

Participants

Conditions

Temperature: 0 °C

Procedure

23 mg (0.90 mmol) of 95% sodium hydride were added at 0° C. to a solution of 163 mg (0.75 mmol) 4-(4-[1,2,3]triazol-1-yl-butyl)-phenol in 4.0 ml N,N-dimethylformamide and stirred for 30 min. at 0° C. 204 mg (0.75 mmol) 5-chloromethyl-2-(4-trifluoromethyl-phenyl)-pyridine (WO 2005/049573) were given to the reaction mixture and stirring continued at r.t for 2 days. After addition of 8 ml water the mixture was stirred for 1 h, the formed precipitate isolated by filtration, washed with water, methanol/water 1:1, and a small amount of ether. The residue was purified by chromatography on silica (eluent: ethyl acetate) to give 240 mg 71% of the title compound as white powder.

Workup

stirringstirring
waitcontinued at r.t for 2 days
stirringwas stirred for 1 h
customthe formed precipitate isolated by filtration
washwashed with water, methanol/water 1:1
customThe residue was purified by chromatography on silica (eluent: ethyl acetate)

Sources & evidence

ORD record: ord-89a19ef0ed494e12aaf6cc388993ebae
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429605B2

Reaction notes

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