Water → HCID 67498772, compound
Reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][OH:8])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]=[N:3]1.[H-].[Na+].Cl[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][N:19]=1.O>C1COCC1>[CH3:25][O:24][C:22](=[O:23])[C:21]1[CH:26]=[CH:27][C:18]([O:8][CH2:7][C:6]2[N:2]([CH3:1])[N:3]=[N:4][C:5]=2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:19][CH:20]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (3-methyl-5-phenyl-3H-[1,2,3]triazol-4-yl)-methanol (189 mg, 1.0 mmol) in THF (3 mL) was added dropwise at 0° C. to a suspension of NaH (55% in oil, 48 mg, 1.1 mmol) in THF (1.5 mL) and the reaction mixture was then stirred at room temperature for 30 min. Then a solution of methyl 6-chloronicotinate (189 mg, 1.1 mmol) in THF (3 mL) was added dropwise at 0° C. and the reaction mixture stirred at room temperature for 20 h. The mixture was then poured into water extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (203 mg, 63%) as an off white solid. MS: m/e=325.2 [M+H]+.
Workup
- stirringthe reaction mixture stirred at room temperature for 20 h
- extractionextracted with ethyl acetate
- washthe combined organic extracts washed with brine
- dry with materialdried over sodium sulphate
- filtrationfiltered
- customevaporated
- customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)
Sources & evidence
- ORD record
- ord-2f922c4d5974476189b9653e02e0c096
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08742097B2
Reaction notes
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