Tetrahydrofuran → HCID 21714327, compound

HRID 1600623Notes

Reaction equation

HRID 1600623 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

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21714308HCID 21714308, compound

Product 1

HCID 21714327HCID 21714327, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

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

Sources & evidence

ORD record
ord-569437ea98e9485fac366d802792a738
Source dataset
uspto-grants-1999_11
Patent number
US05977100

Reaction notes

Loading…