Diisobutylaluminum hydride → HCID 118129967, compound

HRID 2272827Notes

Reaction equation

HRID 2272827 reaction equation
[Br:1][C:2]1[N:14]=[C:5]2[CH:6]=[CH:7][C:8]([C:10](OC)=[O:11])=[CH:9][N:4]2[N:3]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[Br:1][C:2]1[N:14]=[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][OH:11])=[CH:9][N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 1181299972-BroMo-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid Methyl ester

Product 1

HCID 118129967HCID 118129967, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-bromo-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylate (3.0 g, 11.7 mmol) in DCM, is added DIBAL-H (3 equivalents) drop wise at −78° C. and the reaction mixture is warmed to room temperature and stirred for 1 hour. The reaction mixture is quenched with saturated ammonium chloride solution (20 mL) and extracted with DCM (2×50 mL). The combined organic extracts are dried over sodium sulphate, and evaporated. The crude material is triturated with n-pentane to give the title compound as a yellow solid (1.5 g, 57.6%). LCMS m/z 171 (M+H)+.

Workup

  1. customdrop wise at −78° C.
  2. customThe reaction mixture is quenched with saturated ammonium chloride solution (20 mL)
  3. extractionextracted with DCM (2×50 mL)
  4. dry with materialThe combined organic extracts are dried over sodium sulphate
  5. customevaporated
  6. customThe crude material is triturated with n-pentane

Sources & evidence

ORD record
ord-5a760b243ad749569f56692d096053c3
Source dataset
uspto-grants-2015_09
Patent number
US09120793B2

Reaction notes

Loading…