Water → 2-hydroxy-2-methylpropyl 1-(2-hydroxy-2-methylpropyl)-1H-indazole-5-carboxylate

HRID 73096Notes

Reaction equation

HRID 73096 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH3:13][C:14]1([CH3:17])[CH2:16][O:15]1.[C:18]([O-])([O-])=O.[K+].[K+].[OH2:24].CN1[C:30](=O)[CH2:29][CH2:28]C1>>[OH:24][C:29]([CH3:28])([CH3:30])[CH2:18][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH2:13][C:14]([OH:15])([CH3:17])[CH3:16])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

6

Reactant 5

HCID 962WaterHCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 42484541H-Indazole-5-carboxylic acid

Product 1

HCID 668379012-hydroxy-2-methylpropyl 1-(2-hydroxy-2-methylpropyl)-1H-indazole-5-carboxylateYield 62%

Procedure

A mixture of 1H-indazole-5-carboxylic acid (400 mg, 2.47 mmol), 2,2-dimethyloxirane (889 mg, 12.33 mmol) and K2CO3 (1.71 g, 12.33 mmol) in NMP (7 mL) was irradiated with microwave (180° C., 30 min). The mixture was poured into H2O, extracted with EtOAc, dried over Na2SO4, filtered and concentrated. The residual oil was purified by amino gel column chromatography (0-35% EtOAc in hexane) to give 2-hydroxy-2-methylpropyl 1-(2-hydroxy-2-methylpropyl)-1H-indazole-5-carboxylate (468 mg, 62% yield) as a white solid.

Workup

  1. customwas irradiated with microwave (180° C., 30 min)
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residual oil was purified by amino gel column chromatography (0-35% EtOAc in hexane)

Sources & evidence

ORD record
ord-7765fa99a9e1488c84d8e077ba7e8a99
Source dataset
uspto-grants-2014_09
Patent number
US08829026B2

Reaction notes

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