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

HRID 132363Notes

Reaction equation

HRID 132363 reaction equation
[Br: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.[Cl:24]CCl>S(Cl)(Cl)=O>[Br: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:24])=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 59731876(S)-dimethyl 2-((7-bromo-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinate

Product 1

HCID 59732029(S)-dimethyl 2-((7-bromo-4-(chloromethyl)-1H-indazol-5-yl)methyl)succinateYield 99%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

(S)-dimethyl 2-((7-bromo-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinate (2.25 g, 5.8 mmol) was dissolved in 2M thionyl chloride in dichloromethane (42 mL, 84 mmol). Reaction stirred at room temperature for 2.0 hours. Mixture was concentrated. Residue was treated with toluene and then concentrated by roto-vap. Residue was dissolved in ethyl acetate. Mixture was washed twice with aqueous sodium bicarbonate. Organic was dried (magnesium sulfate), filtered and concentrated in vacuo. Title compound was obtained as amber solid in 99% yield. MS m/e (M+H)+=404.9, 403.0, 406.9.

Workup

  1. customReaction
  2. concentrationMixture was concentrated
  3. additionResidue was treated with toluene
  4. concentrationconcentrated by roto-vap
  5. dissolutionResidue was dissolved in ethyl acetate
  6. washMixture was washed twice with aqueous sodium bicarbonate
  7. dry with materialOrganic was dried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a3000ba1da54325a839df428e20f6df
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Reaction notes

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