Potassium Carbonate → 3-(4-chlorophenoxy)-2-methyl-5-(methylthio)-1H-indole-1-acetic acid, methyl ester

HRID 2233748

Reaction equation

[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([S:16][CH3:17])[CH:14]=3)[NH:9][C:8]=2[CH3:18])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30]>CN(C=O)C>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([S:16][CH3:17])[CH:14]=3)[N:9]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:8]=2[CH3:18])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of the product from step (i) (0.45 g), potassium carbonate (0.415 g) and methyl bromoacetate (0.21 ml) in DMF (3 ml) was stirred at 50° C. for 3 h. The reaction was partitioned between ethylacetate/water. The organics were washed with water, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5-15% ethylacetate/iso-hexane. Yield 0.33 g

Workup

customThe reaction was partitioned between ethylacetate/water
washThe organics were washed with water
customdried
customevaporated under reduced pressure
customThe residue was purified by chromatography on silica eluting with 5-15% ethylacetate/iso-hexane

Sources & evidence

ORD record: ord-5bf74929cb0447b38305667a6ff681ba
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709521B2

Linked notes

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