Methanol → (5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methanol

HRID 913840Notes

Reaction equation

HRID 913840 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]([Br:23])[CH:9]=[C:10]2[C:14]=1[N:13]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:12]=[CH:11]2)(=O)C.CO.C(=O)([O-])[O-].[K+].[K+]>>[Br:23][C:8]1[CH:9]=[C:10]2[C:14](=[C:6]([CH2:5][OH:4])[CH:7]=1)[N:13]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:12]=[CH:11]2

Participants

4

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 57546198(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methyl acetate

Product 1

HCID 57546160(5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methanol

Procedure

To a solution of (5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methyl acetate (1.04 g, 2.60 mmol) in methanol (15 mL, 371 mmol) at room temperature was added potassium carbonate (200 mg, 1.45 mmol). After 20 min, the reaction was concentrated and the resulting residue partitioned between water and diethyl ether. The ethereal was washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (12%→25% EtOAc/Hex) gave 0.73 g (78%) as a colorless oil that solidified to an amorphous white solid upon standing. 1H-NMR (CDCl3, 500 MHz) δ 7.91 (s, 1H), 7.81 (d, J=1.5, 1H), 7.43 (d, J=1.8, 1H), 5.90 (s, 2H), 4.97 (d, J=6.4, 2H), 3.49 (m, 2H), 3.43 (t, J=6.4, 1H), 0.83 (m, 2H), −0.09 (s, 9H); 13C NMR(126 MHz, CDCl3) δ ppm 136.7, 133.5, 131.1, 128.1, 125.9, 123.6, 114.4, 80.0, 66.6, 62.5, 17.8, −1.4.

Workup

  1. concentrationthe reaction was concentrated
  2. customthe resulting residue partitioned between water and diethyl ether
  3. washThe ethereal was washed with water (2×)
  4. dry with materialbrine, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customColumn chromatography (12%→25% EtOAc/Hex) gave 0.73 g (78%) as a colorless oil that solidified to an amorphous white solid

Sources & evidence

ORD record
ord-1fcceae6afa8474a86253365968eb453
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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