Sodium hydride → 4-{4-Cyclopropyl-5-[1-(2-m-tolyl-2H-tetrazol-5-yl)-ethoxy]-4H-[1,2,4]triazol-3-yl}-pyridine

HRID 639809Notes

Reaction equation

HRID 639809 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[N:11]=[N:10][C:9]([CH:12]([OH:14])[CH3:13])=[N:8]2)[CH:2]=1.[H-].[Na+].[CH:18]1([N:21]2[C:25](S(C)(=O)=O)=[N:24][N:23]=[C:22]2[C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)[CH2:20][CH2:19]1>>[CH:18]1([N:21]2[C:25]([O:14][CH:12]([C:9]3[N:10]=[N:11][N:7]([C:3]4[CH:2]=[C:1]([CH3:15])[CH:6]=[CH:5][CH:4]=4)[N:8]=3)[CH3:13])=[N:24][N:23]=[C:22]2[C:30]2[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=2)[CH2:20][CH2:19]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 248533921-[2-(3-Methylphenyl)-2H-tetrazol-5-yl]ethanolHCID 578379334-(4-Cyclopropyl-5-methanesulfonyl-4H-[1,2,4]triazol-3-yl)-pyridine

Product 1

HCID 684311094-{4-Cyclopropyl-5-[1-(2-m-tolyl-2H-tetrazol-5-yl)-ethoxy]-4H-[1,2,4]triazol-3-yl}-pyridineYield 19%

Procedure

The title compound (7.8 mg, 19%, clear oil) was prepared from 1-(2-m-tolyl-2H-tetrazol-5-yl)-ethanol (1 mmol), sodium hydride (1.5 mmol) and 4-(4-cyclopropyl-5-methanesulfonyl-4H-[1,2,4]triazol-3-yl)-pyridine (1.25 mmol). 1H NMR (CDCl3) δ (ppm): 8.73 (d, 2H), 7.93 (m, 2H), 7.78 (d, 2H), 7.45 (t, 1H), 7.33 (d, 1H), 6.62 (q, 1H), 3.22 (m, 1H), 2.49 (s, 3H), 2.05 (d, 3H), 1.14 (m, 2H), 1.00 (m, 2H).

Sources & evidence

ORD record
ord-2cbe39826541457c8fc5c5755cb7acf3
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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