Water → 2-Methyl-3-[3-Methyl-4-(4-[1,2,3]triazol-1-yl-butyl)-phenoxymethyl]-6-(3-trifluoromethyl-phenyl)-pyridine

HRID 33499Notes

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[C:23]([CH3:38])=[N:24][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)=[CH:26][CH:27]=1.O>CN(C)C=O>[CH3:38][C:23]1[C:22]([CH2:21][O:19][C:6]2[CH:7]=[CH:8][C:9]([CH2:10][CH2:11][CH2:12][CH2:13][N:14]3[CH:18]=[CH:17][N:16]=[N:15]3)=[C:4]([CH3:3])[CH:5]=2)=[CH:27][CH:26]=[C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:36])([F:37])[F:35])[CH:29]=2)[N:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

30 mg (0.74 mmol) of 60% sodium hydride were added to at 0° C. to a solution of 162 mg (0.70 mmol) 3-methyl-4-(4-[1,2,3]triazol-1-yl-butyl)-phenol in 8.0 ml N,N-dimethylformamide and stirred for 30 min. at 0° C. 200 mg (0.70 mmol) 3-chloromethyl-2-methyl-6-(3-trifluoromethyl-phenyl)-pyridine were given to the reaction mixture and stirring continued at room temperature (r.t.) overnight. After addition of 16 ml water the mixture was stirred for 1 h, the formed precipitate isolated by filtration, washed with water, n-heptane, and ether. The residue was dried at 40° C. in vacuum to give 255 mg (76%) of the title compound as slightly pink powder.

Workup

stirringstirring
customcontinued at room temperature
custom(r.t.) overnight
stirringwas stirred for 1 h
customthe formed precipitate isolated by filtration
washwashed with water, n-heptane, and ether
customThe residue was dried at 40° C. in vacuum

Sources & evidence

ORD record: ord-070e2e793b2d4a3cb7bf238ab7b933c5
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429605B2

Reaction notes

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