Hydrogen Peroxide → HCID 66899434, compound

HRID 2369891Notes

Reaction equation

HRID 2369891 reaction equation
[CH3:1][O:2][CH:3]([O:27][CH3:28])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10](B3OC(C)(C)C(C)(C)O3)=[CH:11][C:12]=2[C:14]([O:16][CH3:17])=[O:15])[CH:7]=[N:6]1.[OH:29]O>CO>[CH3:1][O:2][CH:3]([O:27][CH3:28])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([OH:29])=[CH:11][C:12]=2[C:14]([O:16][CH3:17])=[O:15])[CH:7]=[N:6]1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 66899178HCID 66899178, compound

Product 1

HCID 66899434HCID 66899434, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At room temperature, to a solution of methyl 1-(2,2-dimethoxyethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-7-carboxylate (287 mg, 0.7 mmol) from Step E above in methanol (12 ml) was added 30% hydrogen peroxide (20.0 eq). The reaction mixture was stirred for 3 h, and then quenched with aqueous sodium sulfite. The mixture was extracted with ethyl acetate and washed with water. The organic extract was concentrated in vacuo to give methyl 1-(2,2-dimethoxyethyl)-5-hydroxy-1H-indazole-7-carboxylate as a white solid: 1H NMR (500 MHz, CDCl3) δ 7.96 (s, 1H), 7.50 (d, J=2.5 Hz, 1H), 7.24 (d, J=2.5 Hz, 1H), 4.90 (d, J=5.5 Hz, 2H), 4.86 (s, 1H), 4.52 (t, J=5.5 Hz, 1H), 3.97 (s, 3H), 3.27 (s, 6H); MS (ESI+) m/z 249 (M+H).

Workup

  1. customquenched with aqueous sodium sulfite
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water
  4. extractionThe organic extract
  5. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-574855a75fe54113b99bd3aa3173a3dc
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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