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

HRID 33481Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([OH:19])[CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[N:15]1.Cl[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)=[CH:24][N:23]=1.O>CN(C)C=O>[CH3:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[N:15]1)[O:19][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:36])([F:35])[F:37])=[CH:30][CH:29]=2)=[CH:24][N:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

8.0 mg (0.31 mmol) of 95% sodium hydride were added at 0° C. to a solution of 65 mg (0.28 mmol) 3-methyl-4-(4-[1,2,3]triazol-1-yl-butyl)-phenol in 3.0 ml N,N-dimethylformamide and stirred for 30 min. at 0° C. 76 mg (0.28 mmol) 2-chloromethyl-5-(4-trifluoromethyl-phenyl)-pyridine were given to the reaction mixture and stirring continued at r.t overnight. After addition of 6 ml water the mixture was stirred for 1 h, the formed precipitate isolated by filtration, washed with water, methanol/water 1:1. The residue was purified by chromatography on silica (eluent: ethyl acetate) to give 91 mg (70%) of the title compound as white powder.

Workup

stirringstirring
customcontinued at r.t overnight
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-7b87ca582b674beab5ef911014819cc5
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429605B2

Reaction notes

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