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

HRID 33516Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 97 mg (0.42 mmol) 3-methyl-4-(4-[1,2,3]triazol-1-yl-butyl)phenol in 4.0 ml N,N-dimethylformamide was treated at 0° C. with 18 mg (0.44 mmol) of 60% sodium hydride and stirred at 0° C. for 30 min. Then 100 mg (0.42 mmol) 5-Chloromethyl-2-(4-chloro-phenyl)-pyridine (GB 1147068) were added and stirred continued over night. After addition of 8 ml water, the precipitate was isolated, washed thoroughly with water, methanol/water 1:1 and diisopropylether. The residue was dried at 40° C. to give 133 mg (73%) of the title compound as light brown powder.

Workup

stirringstirred
waitcontinued over night
customthe precipitate was isolated
washwashed thoroughly with water, methanol/water 1:1 and diisopropylether
customThe residue was dried at 40° C.

Sources & evidence

ORD record: ord-8c5587bd30d14917ae8a8a623330eb27
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429605B2

Reaction notes

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