Methanol → HCID 58236998, compound

HRID 1188967Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.CO.[CH3:29][Si](C=[N+]=[N-])(C)C>C(OCC)(=O)C>[CH3:29][O:1][C:2]1[CH:3]=[C:4]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2

Participants

Conditions

Temperature: 4 °C

Procedure

To an ice-cooled and stirred solution of ethyl 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (1.08 g) in ethyl acetate (30 mL)-methanol (8 mL) was added 2M trimethylsilyldiazomethane (diethyl ether solution, 2.8 mL), and the mixture was stirred at 4° C. for 2 h, followed by an addition of 2M trimethylsilyldiazomethane (diethyl ether solution, 2.8 mL). After stirred at 4° C. for 1 h, the reaction mixture was quenched with 1M hydrochloric acid and extracted with ethyl acetate. The organic layer was washed successively with aqueous sodium hydrogen carbonate and brine, dried (MgSO4), filtered, and concentrated to give a light yellow oil, which was crystallized from ethyl acetate-hexane to give the title compound (933 mg, 83%) as pale yellow crystals. mp 161-162° C.

Workup

stirringAfter stirred at 4° C. for 1 h
customthe reaction mixture was quenched with 1M hydrochloric acid
extractionextracted with ethyl acetate
washThe organic layer was washed successively with aqueous sodium hydrogen carbonate and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customto give a light yellow oil, which
customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-3cb8db182cd9409db1b4a4e2a7ad855b
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673942B2

Reaction notes

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