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

HRID 132451

반응식

HRID 132451 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-4ebe9e1909d84e1f955f7ceafbc22d24
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384931B2

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