Methanol → HCID 178500725, compound

HRID 2378921Notes

Reaction equation

HRID 2378921 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]([Cl:29])=[N:9][NH:10]2)(=O)C.CO.C[O-].[Mg+2].C[O-]>>[Br:28][C:12]1[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]([CH2:5][OH:4])=[C:7]2[C:11]=1[NH:10][N:9]=[C:8]2[Cl:29]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 164537Methanol, magnesium salt (2:1)HCID 178471819HCID 178471819, compound

Product 1

HCID 178500725HCID 178500725, compoundYield 96%

Procedure

(S)-Diethyl 2-((4-(acetoxymethyl)-7-bromo-3-chloro-1H-indazol-5-yl)methyl)succinate (550 mg, 1.123 mmol) was dissolved in methanol (15 mL, 370 mmol). 6-10% Magnesium methoxide in methanol (3.4 mL, 2.57 mmol) was added to the mixture. Reaction stirred at room temperature for 18 hours. Reaction was quenched with 6 mL of 1N hydrochloric acid. Mixture stirred at room temperature for 10 minutes. Mixture was concentrated by roto-vap. Residue was suspended in water. Mixture was made basic with aqueous sodium bicarbonate. Material was extracted twice and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as white solid in 96% yield. MS (M−H)−=419.0.

Workup

  1. customReaction
  2. customReaction
  3. customwas quenched with 6 mL of 1N hydrochloric acid
  4. stirringMixture stirred at room temperature for 10 minutes
  5. concentrationMixture was concentrated by roto-vap
  6. extractionMaterial was extracted twice
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d44bb8ec53b543ffb25ec35c159ca88c
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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