Methanol, magnesium salt (2:1) → (S)-dimethyl 2-((3,7-dibromo-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinate

HRID 132451Notes

Reaction equation

HRID 132451 reaction equation
C([O:4][CH2:5][C:6]1[C:14]([CH2:15][C@@H:16]([CH2:22][C:23]([O:25][CH2:26]C)=[O:24])[C:17]([O:19][CH2:20]C)=[O:18])=[CH:13][C:12]([Br:28])=[C:11]2[C:7]=1[C:8]([Br:29])=[N:9][NH:10]2)(=O)C.C[O-].[Mg+2].C[O-]>CO>[Br:29][C:8]1[C:7]2[C:11](=[C:12]([Br:28])[CH:13]=[C:14]([CH2:15][C@@H:16]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:17]([O:19][CH3:20])=[O:18])[C:6]=2[CH2:5][OH:4])[NH:10][N:9]=1

Participants

4

Reactant 2

HCID 164537Methanol, magnesium salt (2:1)HCID 178471818HCID 178471818, compound

Product 1

HCID 178500724(S)-dimethyl 2-((3,7-dibromo-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(S)-Diethyl 2-((4-(acetoxymethyl)-3,7-dibromo-1H-indazol-5-yl)methyl)succinate (540 mg, 1.011 mmol) was dissolved in methanol (12 mL). 6-10% Magnesium methoxide solution in methanol (2.7 mL, 2.041 mmol) was added to the mixture. Reaction stirred at room temperature for 18 hours. Reaction was quenched with 5 mL 1N hydrochloric acid. Mixture stirred at room temperature for 30 minutes. Methanol was removed from the mixture by roto-vap. Residue was dissolved in water and then made basic with aqueous sodium bicarbonate. Material was extracted twice with ethyl acetate and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as white foam in 99% yield. 1H NMR, MS (M−H)−=463.1, 461.1, 465.1.

Workup

  1. customReaction
  2. customReaction
  3. customwas quenched with 5 mL 1N hydrochloric acid
  4. stirringMixture stirred at room temperature for 30 minutes
  5. customMethanol was removed from the mixture by roto-vap
  6. dissolutionResidue was dissolved in water
  7. extractionMaterial was extracted twice with ethyl acetate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4ebe9e1909d84e1f955f7ceafbc22d24
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Reaction notes

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