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

HRID 1985515Notes

Reaction equation

HRID 1985515 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-e654b0c02c764256a981ef35561a37b7
Source dataset
uspto-grants-2009_06
Patent number
US07544680B2

Reaction notes

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