Tetrahydrofuran → HCID 21714327, compound

HRID 355702Notes

Reaction equation

[CH3:1][N:2]([C:6]1[CH:7]=[CH:8][C:9]([C:20]([F:23])([F:22])[F:21])=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11]2)[CH2:3][CH2:4][OH:5].C(N(CC)CC)C.O1CCCC1.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>O>[CH3:1][N:2]([C:6]1[CH:7]=[CH:8][C:9]([C:20]([F:23])([F:22])[F:21])=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11]2)[CH2:3][CH2:4][O:5][S:37]([CH3:36])(=[O:39])=[O:38]

Participants

Conditions

Temperature: -19 °C

Procedure

A mixture of ethyl 7-[N-methyl-N-(2-hydroxyethyl) amino]-4-trifluoromethyl-1H-indole-2-carboxylate (0.37 g, 1.12 mmol), triethylamine (0.25 g, 2.46 mmol) and tetrahydrofuran (20 ml) was cooled to -19° C., after which methanesulfonyl chloride (0.14 g, 1.23 mmol) was added dropwise with stirring. The reaction mixture was stirred at -18° C. to -13° C. for 1 hour, poured into cold water, and then extracted three times with ethyl acetate. The extract solution was washed with a 5% aqueous sodium hydrogencarbonate solution and a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain an oil of ethyl 7-[N-methyl-N-(2-methanesulfonyloxyethyl)amino]-4-trifluoromethyl-1H-indole-2-carboxylate.

Workup

stirringThe reaction mixture was stirred at -18° C. to -13° C. for 1 hour
extractionextracted three times with ethyl acetate
washThe extract solution was washed with a 5% aqueous sodium hydrogencarbonate solution
dry with materiala 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-5f89256dbd454e5dbdc6d0fe54e99975
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05834454

Reaction notes

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