Sodium borohydride → (5-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methanol

HRID 913913Notes

Reaction equation

HRID 913913 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]=[O:12])[C:8]2[C:4](=[CH:5][N:6]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:7]=2)[CH:3]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:10]=[C:9]([CH2:11][OH:12])[C:8]2[C:4](=[CH:5][N:6]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:7]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 575462315-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole-7-carbaldehyde

Product 1

HCID 57546244(5-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole-7-carbaldehyde (3 g, 9.65 mmol) in ethanol (20 mL) at 0° C. was added sodium borohydride (0.183 g, 4.83 mmol). The ice bath was removed and stirring continued for 1 h. The reaction was recooled to 0° C. and quenched by the cautious addition of saturated ammonium chloride. The reaction was concentrated to remove most of the ethanol. The resulting residue was dissolved in water and extracted with diethyl ether (2×). The ethereal was washed with water, then brine, dried over magnesium sulfate, and concentrated to give 3.3 g (quant.) as a viscous oil. 1H-NMR (CDCl3, 500 MHz) δ 8.04 (s, 1H), 7.55 (d, J=1.5 Hz, 1H), 7.19 (d, J=1.2 Hz, 1H), 5.67 (s, 2H), 5.04 (d, J=4.9 Hz, 2H), 3.61 (t, J=8.2 Hz, 2H), 3.31 (m, 1H), 0.92 (t, J=8.2 Hz, 2H), −0.04 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 145.9, 132.4, 128.0, 124.7, 122.7, 122.6, 118.3, 81.9, 67.8, 62.3, 17.9, −1.4. Mass spec.: 313.12 (MH)+.

Workup

  1. customThe ice bath was removed
  2. customwas recooled to 0° C.
  3. customquenched by the cautious addition of saturated ammonium chloride
  4. concentrationThe reaction was concentrated
  5. customto remove most of the ethanol
  6. dissolutionThe resulting residue was dissolved in water
  7. extractionextracted with diethyl ether (2×)
  8. washThe ethereal was washed with water
  9. dry with materialbrine, dried over magnesium sulfate
  10. concentrationconcentrated
  11. customto give 3.3 g (quant.) as a viscous oil

Sources & evidence

ORD record
ord-8ae5816577da491c86c8d13071d7223a
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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