Sodium borohydride → 5-(trifluoromethyl)-1H-indazole-7-carbaldehyde

HRID 913809Notes

Reaction equation

HRID 913809 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH2:12][OH:13])[CH:11]=1)[N:8](COCC[Si](C)(C)C)[N:7]=[CH:6]2.FC(F)(F)C1C=C2C(=C(C=O)C=1)N(COCC[Si](C)(C)C)N=C2.[BH4-].[Na+]>C(O)C>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH:12]=[O:13])[CH:11]=1)[NH:8][N:7]=[CH:6]2

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 575460585-(Trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1h-indazole-7-carbaldehydeHCID 57546212(5-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methanol

Product 1

HCID 575462105-(trifluoromethyl)-1H-indazole-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

(5-(Trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methanol To a solution of 5-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-7-carbaldehyde (1 g, 2.9 mmol) in ethanol (15 mL) at 0° C. was added sodium borohydride (0.055 g, 1.45 mmol). The ice bath was removed and stirring continued for 15 min. The reaction was cooled to 0° C. and quenched by addition of saturated ammonium chloride. The reaction was concentrated to remove most of the ethanol and poured into diethyl ether. The ethereal was washed with water (2×), then brine, dried over magnesium sulfate, and concentrated to give 0.985 g (98%) as an oil which solidified upon standing. 1H-NMR (CDCl3, 500 MHz) δ 8.08 (s, 1H), 8.00 (s, 1H), 7.57 (d, J=1.2 Hz, 1H), 5.96 (s, 2H), 5.07 (s, 2H), 3.53 (m, 2H), 3.34 (bs, 1H), 0.85 (m, 2H), −0.08 (s, 9H); 13C-NMR (CDCl3, 126 MHz) δ 139.0, 135.1, 125.9, 125.3, 124.52 (q, J=272 Hz), 124.51, 124.2 (q,J=33 Hz), 119.3, 80.1, 66.7, 62.6, 17.8, −1.5.

Workup

  1. customThe ice bath was removed
  2. customquenched by addition of saturated ammonium chloride
  3. concentrationThe reaction was concentrated
  4. customto remove most of the ethanol
  5. additionpoured into diethyl ether
  6. washThe ethereal was washed with water (2×)
  7. dry with materialbrine, dried over magnesium sulfate
  8. concentrationconcentrated
  9. customto give 0.985 g (98%) as an oil which

Sources & evidence

ORD record
ord-44f8da4e166d4d0db8d75b0e6134e8d3
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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