tert-Butanol → HCID 69731332, compound

HRID 1814369Notes

Reaction equation

HRID 1814369 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH2:10]1[O:13][C@H:11]1[CH3:12].CC(C)([O-])C.[K+].CC(O)(C)C>C1COCC1>[N:1]1([CH2:10][C@H:11]([CH3:12])[OH:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 92211H-IndazoleHCID 146262(2S)-2-MethyloxiraneHCID 23665647Potassium tert-butoxide

Product 1

HCID 69731332HCID 69731332, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.5 g (4.23 mmol) indazole, 0.3 mL (S)-propylene oxide (4.4 mmol), 0.53 g potassium t-butoxide (4.3 mmol) and 15 mL of 25:1 t-BuOH:THF was stirred in a sealed tube at 70° C. overnite. The solvent was removed in vacuo, 50 mL ethyl acetate was added to the residue, the mixture was filtered, concentrated and the residue purified by chromatography over silica eluting with 1:1 EtOAc:hexanes to yield 0.250 g (1.42 mmol, 67%) of the title compound as a viscous oil. MS (APCI) m/z 177 (M+1).

Workup

  1. customThe solvent was removed in vacuo, 50 mL ethyl acetate
  2. additionwas added to the residue
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated
  5. customthe residue purified by chromatography over silica eluting with 1:1 EtOAc

Sources & evidence

ORD record
ord-c9e43ffe6ec548a49a6947d2df400bad
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

Loading…