Sodium borohydride → HCID 57546126, compound

HRID 913821Notes

Reaction equation

HRID 913821 reaction equation
[Br:1][C:2]1[N:3]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:4]=[C:5]2[C:10]=1[CH:9]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:7]=[C:6]2[CH:15]=[O:16].BrC1N(COCC[Si](C)(C)C)N=C2C=1C=C(C(F)(F)F)C=C2CO.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[N:3]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:4]=[C:5]2[C:10]=1[CH:9]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:7]=[C:6]2[CH:15]=[O:16]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86626240HCID 86626240, compound

Product 1

HCID 57546126HCID 57546126, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

(3-Bromo-5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methanol 3-Bromo-5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole-7-carbaldehyde (400 mg, 0.95 mmol) was suspended in ethanol (5 mL), cooled to 0° C., and treated sodium borohydride (18 mg, 0.47 mmol) in one portion. Cooling was removed and the reaction stirred at room temperature for 1 h. The reaction was cooled to 0° C. and treated with saturated aqueous ammonium chloride. The reaction was concentrated to remove most of the ethanol and diluted with ethyl acetate. The layers were separated and the organic layer washed with brine (2×), dried over sodium sulfate, filtered and concentrated. Flash chromatography on silica gel afforded 220 mg (55%) as a light yellow oil. 1H-NMR (CDCl3, 300 MHz) δ 7.86 (s, 1H), 7.61 (s, 1H), 5.86 (s, 2H), 5.02 (s, 2H), 3.51-3.56 (m, 2H), 0.79-0.85 (m, 2H), 0.09 (s, 9H). Mass spec.: 448.82 (MNa)+.

Workup

  1. temperatureCooling
  2. customwas removed
  3. temperatureThe reaction was cooled to 0° C.
  4. additiontreated with saturated aqueous ammonium chloride
  5. concentrationThe reaction was concentrated
  6. customto remove most of the ethanol
  7. additiondiluted with ethyl acetate
  8. customThe layers were separated
  9. washthe organic layer washed with brine (2×)
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customFlash chromatography on silica gel afforded 220 mg (55%) as a light yellow oil

Sources & evidence

ORD record
ord-3c4e6a10d28746a8a963e3412c2c930f
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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