HCID 57546081, compound → HCID 57546099, compound

HRID 913867Notes

Reaction equation

HRID 913867 reaction equation
[F: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.[CH3:21][Mg]Br>O1CCCC1>[F:1][C:2]1[CH:10]=[C:9]([CH:11]([OH:12])[CH3:21])[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 57546081HCID 57546081, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57546099HCID 57546099, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-fluoro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole-7-carbaldehyde (1.53 g, 5.2 mmol) in tetrahydrofuran (32 mL) at −78° C. was added methyl magnesiumbromide (3M in diethyl ether, 3.46 mL, 10.4 mmol). The reaction was allowed to gradually warm in the ice bath (ca. 2 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 1.59 g (99%) as an yellow oil. 1H-NMR (CDCl3, 500 MHz) δ 8.05(s, 1H), 7.15(m, 1H), 7.05(m, 1H), 5.68(s, 2H), 5.33(q, J=5 Hz, 1H), 3.63(m, 2H), 1.68 (d, J=10.0 Hz, 3H), 0.93(m, 2H), −0.03(s, 9H); 13C-NMR (CDCl3, 126MHz) δ 58.7 (d, J=960 Hz), 144.4, 137.7, 122.9, 121.9, 113.5, 113.3, 101.6, 101.4, 81.9, 68.0, 67.6, 25.7, 23.3, 17.9, −1.38; Mass spec.: 311.33 (MH)+.

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 1.59 g (99%) as an yellow oil

Sources & evidence

ORD record
ord-e5b5f5db548b4f8a96a90be082796261
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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