Sodium hydride → 3-[({[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]methyl}oxy)methyl]benzonitrile

HRID 606467Notes

Reaction equation

[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH:12]=[N:11][C:10]([CH2:13][OH:14])=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[C:32]#[N:33].[H-].[Na+]>C1COCC1>[C:21]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:8]2[CH:12]=[N:11][C:10]([CH2:13][O:14][CH2:28][C:29]3[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=3)[C:32]#[N:33])=[N:9]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of [1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]methanol obtained in Reference Example 36 (3.00 g, 8.79 mmol), 3-(bromomethyl)benzonitrile (1.89 g, 9.67 mmol) and 60% sodium hydride (oil dispersion, 0.316 g, 13.2 mmol) in THF (100 mL) was stirred at 70° C. for 15 hr. The reaction mixture was cooled to room temperature, and extracted with water and ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (10-30% ethyl acetate/hexane) to give the title compound as a colorless oil (3.50 g, 87%).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with water and ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (10-30% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-0c3e3a2fbce9499bbea021a0575ccbc5
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915267B2

Reaction notes

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