Toluene → HCID 21194584, compound

HRID 565066Notes

Reaction equation

CO[C:3]1O[C:5](OC)=[CH:6][CH:7]=1.[NH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:29]([F:32])([F:31])[F:30])=[C:18]2[C:22]=1[N:21]([CH3:23])[C:20]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19]2.C1(C)C=CC=CC=1>C(O)(=O)C>[CH3:23][N:21]1[C:22]2[C:18](=[C:17]([C:29]([F:32])([F:30])[F:31])[CH:16]=[CH:15][C:14]=2[O:13][CH2:12][CH2:11][N:10]2[CH:3]=[CH:7][CH:6]=[CH:5]2)[CH:19]=[C:20]1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

Conditions

Temperature: 70 °C

Procedure

After 1.28 g (9.69 mmol) of 2,5-dimethoxyfuran was added to a solution of 2.91 g (8.81 mmol) of ethyl 7-(2-aminoethoxy)-1-methyl-4-trifluoromethyl-2-indolecarboxylate in 30 ml of acetic acid, the mixture was stirred at 50° C. for 4 hours and at 70° C. for further an hour. Toluene was added to the reaction mixture followed by concentration under reduced pressure. Ice water was poured onto the resulting residue. The mixture was then extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography to give 1.96 g of ethyl 1-methyl-7-[2-(1H-pyrrol-1-yl)ethoxy]-4-trifluoromethyl-2-indolecarboxylate.

Workup

concentrationfollowed by concentration under reduced pressure
additionIce water was poured onto the resulting residue
extractionThe mixture was then extracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-61c68c2c376148d0853ae548031c9c95
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06169107A

Reaction notes

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