HCID 86606423, compound → HCID 59810807, compound

HRID 2240168Notes

Reaction equation

HRID 2240168 reaction equation
[CH3:1][Mg]Cl.[CH2:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15](N(OC)C)=[O:16])=[CH:12][CH:13]=2)[N:8]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[N:7]=1)[CH3:5]>O1CCCC1>[CH2:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15](=[O:16])[CH3:1])=[CH:12][CH:13]=2)[N:8]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:26])([CH3:27])[CH3:28])[N:7]=1)[CH3:5]

Participants

4

Reactant 2

HCID 86606423HCID 86606423, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 59810807HCID 59810807, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium chloride (7.7 mL, 3M in tetrahydrofuran) was added dropwise at −78° C. under an atmosphere of argon to a solution of 3-Ethyl-N-methoxy-N-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole-6-carboxamide (4.0 g, 0.011 mol) in tetrahydrofuran (114 mL). The resulting mixture was allowed to warm slowly to room temperature. The reaction was then quenched by the addition of a saturated solution of ammonium chloride. Ethyl acetate (150 mL) and water (100 mL) were then added, and the organic layer was separated, washed with water and with brine, and then dried (sodium sulfate). After filtration, the solvent was concentrated, and the residue was purified by column chromatography on silica gel, eluting with a gradient of 50% ethyl acetate in hexanes to 100% ethyl acetate over 30 minutes, to give 3.5 g (quantitative yield) of 1-(3-Ethyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-6-yl)ethanone. 1H NMR (CDCl3) δ 0.0 (m, 1H), 1.0 (t, 3H), 1.1-1.4 (m, 2H), 2.7 (s, 3H), 2.9-3.1 (m, 2H), 3.5 (1, 2H), 5.7 (s, 2H), 7.5 (m, 2H), 8.0 (s, 1H).

Workup

  1. customThe reaction was then quenched by the addition of a saturated solution of ammonium chloride
  2. additionEthyl acetate (150 mL) and water (100 mL) were then added
  3. customthe organic layer was separated
  4. washwashed with water and with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationAfter filtration
  7. concentrationthe solvent was concentrated
  8. customthe residue was purified by column chromatography on silica gel
  9. washeluting with a gradient of 50% ethyl acetate in hexanes to 100% ethyl acetate over 30 minutes

Sources & evidence

ORD record
ord-eac8289957004fafa446bae97190a7da
Source dataset
uspto-grants-2010_05
Patent number
US07723348B2

Reaction notes

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