Water → 1H-Indazole-1-carboxylic acid, 6-(hydroxymethyl)-, 1,1-dimethylethyl ester

HRID 878554Notes

Reaction equation

HRID 878554 reaction equation
[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10](OC)=[O:11])[CH:8]=2)[CH:3]=[N:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[OH:11][CH2:10][C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[N:2][N:1]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 594908731-tert-Butyl 6-methyl 1H-indazole-1,6-dicarboxylate

Product 1

HCID 594908841H-Indazole-1-carboxylic acid, 6-(hydroxymethyl)-, 1,1-dimethylethyl esterYield 14.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-tert-butyl 6-methyl 1H-indazole-1,6-dicarboxylate (766 mg, 2.76 mmol) in anhydrous THF (11 mL) was cooled to −30° C., LiAlH4 (210 mg, 5.53 mmol) was added in portions below −30° C., and the mixture was stirred at this temperature for 1.5 h, added water:10% NaOH: water=0.8 mL: 2.4 mL: 0.8 mL carefully, filtered, and the filtrate was concentrated and purified by silica gel chromatograph to afford 100 mg of the title compound (14%). 1H NMR (400 MHz, CDCl3): δ 1.72 (9H, s), 4.86 (2H, s), 7.33 (1H, d, J=8.0 Hz), 7.69 (1H, d, J=8.4 Hz), 8.13 (1H, s), 8.21 (1H, s). [M+H] Calc'd for C13H16N2O3, 249; Found, 249.

Workup

  1. filtration10% NaOH: water=0.8 mL: 2.4 mL: 0.8 mL carefully, filtered
  2. concentrationthe filtrate was concentrated
  3. custompurified by silica gel chromatograph

Sources & evidence

ORD record
ord-01370a0eb7004fc7a73b2cd6cc8e9262
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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