Diisobutylaluminum hydride → (2-(2,6-Dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl)methanol

HRID 2272829Notes

Reaction equation

HRID 2272829 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:21]=[C:12]2[CH:13]=[CH:14][C:15]([C:17](OC)=[O:18])=[CH:16][N:11]2[N:10]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:21]=[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][OH:18])=[CH:16][N:11]2[N:10]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 118129983Methyl 2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylate

Product 1

HCID 118129975(2-(2,6-Dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl)methanolYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylate (0.35 g, 1.24 mmol) in DCM (20 mL), DiBAL-H (1 M solution in toluene, 4.98 mL, 4.98 mmol) is added drop wise at 0° C. The reaction mixture is warmed to room temperature and stirred for 2 hours. The reaction is quenched with aqueous NH4Cl solution and extracted with EtOAc (4×50 mL). The combined extracts are dried over sodium sulphate, filtered, and concentrated. The crude material is purified by silica gel chromatography (combiflash) eluting with 50% EtOAc in hexanes. The product is concentrated to give the title compound as a transparent liquid (0.18 g, 57%). LCMS m/z 254 (M+H)+.

Workup

  1. customThe reaction is quenched with aqueous NH4Cl solution
  2. extractionextracted with EtOAc (4×50 mL)
  3. dry with materialThe combined extracts are dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material is purified by silica gel chromatography (combiflash)
  7. washeluting with 50% EtOAc in hexanes
  8. concentrationThe product is concentrated

Sources & evidence

ORD record
ord-d5d5fb1c13c2488ba7906c78afe4b8e7
Source dataset
uspto-grants-2015_09
Patent number
US09120793B2

Reaction notes

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