Tin tetrachloride → HCID 22627276, compound

HRID 1108695Notes

Reaction equation

HRID 1108695 reaction equation
[CH2:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[CH:7]=2)[CH2:2][CH3:3].[Sn](Cl)(Cl)(Cl)Cl.[CH3:22][O:23][CH2:24][C:25](Cl)=[O:26]>ClCCl>[CH3:22][O:23][CH2:24][C:25]([C:12]1[C:11]2[C:6](=[CH:7][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:10]=2)[NH:5][C:4]=1[CH2:1][CH2:2][CH3:3])=[O:26]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 96623Methoxyacetyl chlorideHCID 22627295Methyl 2-propylindole-6-carboxylate

Product 1

HCID 22627276HCID 22627276, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 2-propylindole-6-carboxylate (300 mg) in dichloromethane (10 ml) was added a 1M solution of tin(IV) chloride in dichloromethane (2.76ml) at 20° C. The mixture was stirred at 20° C. for 30 minutes, then methoxyacetyl chloride (0.25 ml) was added. After stirred at 20° C. for 30 minutes, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:10-1:1) to give methyl 3-methoxyacetyl-2-propylindole-6-carboxylate (135 mg) as pale yellow crystals.

Workup

  1. stirringAfter stirred at 20° C. for 30 minutes
  2. customthe mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:10-1:1)

Sources & evidence

ORD record
ord-499bea01b0984e47ab7c5d1a17539910
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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