Tin tetrachloride → HCID 22627276, compound

HRID 278081Notes

Reaction equation

HRID 278081 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 (2.76 ml) 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. or 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. or 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-476294f71561446a8abf351080d5b188
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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