5-(Trifluoromethyl)-2-[[2-(trimethylsilyl)ethoxy]methyl]-2H-indazole-7-carboxaldehyde → HCID 57546130, compound

HRID 913815Notes

Reaction equation

HRID 913815 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:11]=[C:10]([CH:12]=[O:13])[C:9]2[C:5](=[CH:6][N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:8]=2)[CH:4]=1.[CH3:24][Mg]Br>O1CCCC1>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:11]=[C:10]([CH:12]([OH:13])[CH3:24])[C:9]2[C:5](=[CH:6][N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:19])([CH3:20])[CH3:21])[N:8]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 575459555-(Trifluoromethyl)-2-[[2-(trimethylsilyl)ethoxy]methyl]-2H-indazole-7-carboxaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 57546130HCID 57546130, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole-7-carbaldehyde (0.5 g, 1.45 mmol) in tetrahydrofuran (10 mL) at −78° C. was added methyl magnesiumbromide (3 M in diethyl ether, 0.97 mL, 2.90 mmol). The reaction was allowed to gradually warm in the ice bath (ca. 1 h) to 0° C. The reaction which had been a suspension became a solution. The reaction was quenched by addition of saturated ammonium chloride and poured into diethyl ether. The ethereal was washed with water (2×), then brine, dried over magnesium sulfate, and concentrated to give 444 mg (85%) as an oil. 1H-NMR (CDCl3, 500 MHz) δ 8.23 (s, 1H), 7.93 (s, 1H), 7.39 (s, 1H), 5.73 (s, 2H), 5.38 (q, J=6.4 Hz, 1H), 3.65 (m, 2H), 3.52 (bs, 1H), 1.71 (d, J=6.7 Hz, 3H), 0.94 (m, 2H), −0.03 (s, 9H); 13C-NMR (CDCl3, 126 MHz) δ 147.3, 136.6, 128.0, 124.8, 124.7 (q, J=273 Hz), 124.7 (q, J=32 Hz), 121.3, 118.4 (q, J=4.8 Hz), 117.4 (q, J=2.9 Hz), 82.1, 68.2, 68.0, 23.4, 17.9, −1.4.

Workup

  1. customThe reaction which
  2. customThe reaction was quenched by addition of saturated ammonium chloride
  3. additionpoured into diethyl ether
  4. washThe ethereal was washed with water (2×)
  5. dry with materialbrine, dried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give 444 mg (85%) as an oil

Sources & evidence

ORD record
ord-cb6ab62bd201401bb86fbcdbfb37d946
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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