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

HRID 132462Notes

Reaction equation

HRID 132462 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]([Cl:28])=[C:11]2[C:7]=1[C:8]([Cl:29])=[N:9][NH:10]2)(=O)C.C[O-].[Mg+2].C[O-]>CO>[Cl:29][C:8]1[C:7]2[C:11](=[C:12]([Cl: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 178471822HCID 178471822, compound

Product 1

HCID 178500726(S)-dimethyl 2-((3,7-dichloro-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinateYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(S)-Diethyl 2-((4-(acetoxymethyl)-3,7-dichloro-1H-indazol-5-yl)methyl)succinate (1.30 g, 2.92 mmol) was dissolved in methanol (45 mL). 6-10% Magnesium methoxide in methanol (8.4 mL, 6.35 mmol) was added to the mixture. Reaction stirred at room temperature for 16 hours. Reaction was quenched with 14 mL 1N hydrochloric acid. Methanol was removed from the mixture by roto-vap. Residue was treated with aqueous sodium bicarbonate. Material was extracted twice with ethyl acetate and the aqueous phase was discarded. The combined organic phases were washed with water and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as dark amber oil in 91% yield. MS (M−H)−=373.0, 375.0.

Workup

  1. customReaction
  2. customReaction
  3. customwas quenched with 14 mL 1N hydrochloric acid
  4. customMethanol was removed from the mixture by roto-vap
  5. additionResidue was treated with aqueous sodium bicarbonate
  6. extractionMaterial was extracted twice with ethyl acetate
  7. washThe combined organic phases were washed with water
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-54eca71df4ec46e9ad77b666336deb42
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Reaction notes

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