Sodium hydride → HCID 11530622, compound

HRID 639804Notes

Reaction equation

HRID 639804 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+].CS([C:22]1[N:23]([CH3:33])[C:24]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)=[N:25][N:26]=1)(=O)=O>>[CH3:33][N:23]1[C:22]([O:14][CH:12]([C:9]2[N:10]=[N:11][N:7]([C:3]3[CH:2]=[C:1]([CH3:15])[CH:6]=[CH:5][CH:4]=3)[N:8]=2)[CH3:13])=[N:26][N:25]=[C:24]1[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 221514774-[5-(Methanesulfonyl)-4-methyl-4H-1,2,4-triazol-3-yl]pyridineHCID 248533921-[2-(3-Methylphenyl)-2H-tetrazol-5-yl]ethanol

Product 1

HCID 11530622HCID 11530622, compoundYield 80.5%

Procedure

The title compound (70 mg, 79%, off-white solid) was prepared from 1-(2-m-tolyl-2H-tetrazol-5-yl)-ethanol (50.3 mg, 0.24 mmol), sodium hydride (16 mg, 0.4 mmol) and 4-(5-methanesulfonyl-4-methyl-4H-[1,2,4]triazol-3-yl)-pyridine (70.2 mg, 0.30 mmol). The product was purified by chromatography using a silica SPE tube (2.5-4% methanol in dichloromethane). 1H NMR (CDCl3) δ (ppm): 8.76 (br.d, 2H), 7.95 (s, 1H), 7.94 (d, 1H), 7.62 (d, 2H), 7.44 (t, 1H), 7.32 (d, 1H), 6.61 (q, 1H), 3.63 (s, 3H), 2.28 (s, 3H), 2.04 (d, 3H).

Workup

  1. customThe product was purified by chromatography

Sources & evidence

ORD record
ord-b676eff8528e466b92bbef67d559a06c
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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