Sodium Iodide → Ethyl 1-methyl-3-[(1-methylethyl)thio]-5-(phenylmethoxy)-methoxy-1H-indole-2-carboxylate

HRID 21594Notes

Reaction equation

C[N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[C:4]([S:19]([CH:21]([CH3:23])[CH3:22])=O)=[C:3]1[C:24]([O:26][CH2:27][CH3:28])=[O:25].[I-].[Na+].F[C:32](F)(F)[C:33](OC(=O)C(F)(F)F)=[O:34]>O1CCCC1>[CH3:32][CH2:33][O:34][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[C:4]([S:19][CH:21]([CH3:22])[CH3:23])=[C:3]1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of ethyl 1-methyl-3-[(1-methylethyl)sulfinyl]-5-(phenylmethoxy)-1H-indole-2-carboxylate (0.50 g, 1.3 mmol) and sodium iodide (0.69 g, 4.6 mmol) in 30 mL of tetrahydrofuran is cooled to 0° C. and treated dropwise with trifluoroacetic anhydride (1.0 mL, 1.5 g, 7.1 mmol). The mixture is stirred for 10 minutes, then quenched by pouring into 100 mL of cold 5% aqueous sodium bicarbonate solution. The mixture is extracted with ether, and the combined organic layers are washed with 5% aqueous sodium thiosulfate solution, followed by brine. The organic layer is dried (anhydrous magnesium sulfate) and evaporated to give 0.44 g (92%) of product; mp 94°-96° C.

Workup

customquenched
additionby pouring into 100 mL of cold 5% aqueous sodium bicarbonate solution
extractionThe mixture is extracted with ether
washthe combined organic layers are washed with 5% aqueous sodium thiosulfate solution
dry with materialThe organic layer is dried (anhydrous magnesium sulfate)
customevaporated

Sources & evidence

ORD record: ord-de1ef4a3a324441aa786e107d1e81295
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424329

Reaction notes

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