Sodium hydride → ethyl 2-[5-[(3,5-dibutyl-1H-1,2,4-triazol-1-yl)methyl]-2-pyridinyl]benzoate

HRID 466200Notes

Reaction equation

[CH2:1]([C:5]1[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH3:13])[NH:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[H][H].Br[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=2[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:24][CH:25]=1>CN(C=O)C>[CH2:1]([C:5]1[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH3:13])[N:7]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=3[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:24][CH:25]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Under nitrogen, 630 mg (3.5 mmol) of 3,5-dibutyl-1H-1,2,4-triazole from step 3 of Example 1 was added in small portions to 5.4 mmol of sodium hydride in 8 mL of DMF; stirring was continued until hydrogen evolution had ceased. The anion solution was cooled to 0° C. and treated with a solution of the crude ethyl 2-(5-bromomethyl-2-pyridinyl)benzoate from step 7 in 10 mL of DMF. The reaction was stirred at ambient temperature overnight, quench with 1 mL of absolute ethanol, and concentrated in vacuo; the resulting residue was redisolved in methylene chloride, filtered, and reconcentrated in vacuo to give crude ethyl 2-[5-[(3,5-dibutyl-1H-1,2,4-triazol-1-yl)methyl]-2-pyridinyl]benzoate.

Workup

stirringThe reaction was stirred at ambient temperature overnight
customquench with 1 mL of absolute ethanol
concentrationconcentrated in vacuo
filtrationfiltered

Sources & evidence

ORD record: ord-43333f38f6e84a3d8c925b2e0461991e
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05155117

Reaction notes

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