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

HRID 2378898Notes

Reaction equation

HRID 2378898 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(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.

Workup

  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 Title compound
  7. customwas obtained as amber solid in 99% yield

Sources & evidence

ORD record
ord-6b722a61eae34dd0bdf67dab7a5322d2
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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