HCID 57546121, compound → HCID 57546015, compound

HRID 913861Notes

Reaction equation

HRID 913861 reaction equation
[CH3:1][O:2][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.[CH3:22][Mg]Br>O1CCCC1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH:12]([OH:13])[CH3:22])[C:9]2[C:5](=[CH:6][N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:19])[CH3:21])[N:8]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 57546121HCID 57546121, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57546015HCID 57546015, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-methoxy-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole-7-carbaldehyde (1.32 g, 4.31 mmol) in tetrahydrofuran (27 mL) at −78° C. was added methyl magnesiumbromide (3M in diethyl ether, 2.87 mL, 8.62 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 1.44 g (quant.) as oil. 1H-NMR (CDCl3, 300 MHz) δ 7.92 (s, 1H), 6.88 (s, 1H), 6.75 (s, 1H), 5.63 (s, 2H), 5.26 (q, J=6 Hz, 1H), 3.8 (s, 3H), 3.6 (m, 2H), 1.65 (d, J=6 Hz, 3H), 0.9 (m, 2H), -0.06 (s, 9H); Mass spec.: 323.42 (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 1.44 g (quant.) as oil

Sources & evidence

ORD record
ord-30a4e2bdcf504980ba1ed6ce36a5ed8a
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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