Thionyl Chloride → (S)-dimethyl 2-((7-methyl-4-(chloromethyl)-1H-indazol-5-yl)methyl)succinate

HRID 132434Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132434
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:13][C@@H:14]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:15]([O:17][CH3:18])=[O:16])[C:5]([CH2:11]O)=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.S(Cl)([Cl:26])=O>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:13][C@@H:14]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:15]([O:17][CH3:18])=[O:16])[C:5]([CH2:11][Cl:26])=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 59731874(S)-dimethyl 2-((7-methyl-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinate

Produkt 1

HCID 67318680(S)-dimethyl 2-((7-methyl-4-(chloromethyl)-1H-indazol-5-yl)methyl)succinateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(S)-dimethyl 2-((7-methyl-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinate (180 mg, 0.56 mmol) was dissolved in dichloromethane (4.0 mL). 2M Thionyl chloride in dichloromethane (4.0 mL, 8.0 mmol) was added to the mixture. Reaction stirred at room temperature for 2.5 hours. Mixture was concentrated. Residue was treated with toluene and then concentrated by roto-vap. Residue was dissolved in dichloromethane and then concentrated to dryness. Title compound was obtained as amber solid in 99% yield. MS m/e (M+H)+=339.1.

Aufarbeitung

  1. customReaction
  2. concentrationMixture was concentrated
  3. additionResidue was treated with toluene
  4. concentrationconcentrated by roto-vap
  5. dissolutionResidue was dissolved in dichloromethane
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-bee656fdd3e04c1996cd661a709daefc
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384931B2

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