Potassium Carbonate → 1H-4-indolyl 2-[3-(1H-3-indolyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]ethyl ether

HRID 987568Notes

Reaction equation

[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][C:3]([C:9]1[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=1)=[CH:2]2.Cl[CH2:19][CH2:20][O:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:23]=1[CH:24]=[CH:25][NH:26]2.C([O-])([O-])=O.[K+].[K+]>CC#N>[NH:26]1[C:27]2[C:23](=[C:22]([O:21][CH2:20][CH2:19][N:8]3[CH:5]4[CH2:6][CH2:7][CH:1]3[CH:2]=[C:3]([C:9]3[C:17]5[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=5)[NH:11][CH:10]=3)[CH2:4]4)[CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:25]1

Participants

Conditions

Temperature: 80 °C

Procedure

To 200 mg (0.89 mmol) 3-(8-aza-bicyclo[3.2.1]oct-2-en-3-yl)-1H-indole, 174 mg (0.89 mmol) 4-(2-chloroethoxy)-1H-indole and 10 mL MeCN is added 246 mg (1.78 mmol) K2CO3. After heating at 80° C. for 12 h, the reaction mixture is cooled to 23° C., filtered through celite and evaporated to a light yellow oil. Flash chromatography on SiO2 gel, eluting with CHCl3/MeOH (20/1 to 10/1), gives 208 mg (0.54 mmol, a 61% yield) of the title compound as an off-white solid. The corresponding oxalate salt is prepared by combining the title compound with 1 equivalent of oxalic acid in EtOH/Et2O. The oxalate salt of the title compound precipitates as an off-white solid. Recrystallization from EtOH/Et2O gives the oxalate salt of the title compound as an off-white solid. mp: 135-138° C.; MS (ES) m/z 384 (MH)+.

Workup

temperaturethe reaction mixture is cooled to 23° C.
filtrationfiltered through celite
customevaporated to a light yellow oil
washFlash chromatography on SiO2 gel, eluting with CHCl3/MeOH (20/1 to 10/1)
customgives 208 mg (0.54 mmol

Sources & evidence

ORD record: ord-ed0c0398fca24c1d9dad2bdb380cb392
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06632824B2

Reaction notes

Loading…