Pyridine → 1-(4-Isopropoxyphenyl)-5-(5-(trifluoromethyl)pyrid-2-yl)indole-2-carboxylic acid ethyl ester
Reaction equation
CCN(CC)CC.N1C=CC=CC=1.[CH2:14]([O:16][C:17]([C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][N:29]=1)=[CH:23][CH:22]=2)=[O:18])[CH3:15].[CH:38]([O:41][C:42]1[CH:47]=[CH:46][C:45](B(O)O)=[CH:44][CH:43]=1)([CH3:40])[CH3:39]>CC([O-])=O.CC([O-])=O.[Cu+2].C(Cl)Cl>[CH2:14]([O:16][C:17]([C:19]1[N:20]([C:45]2[CH:46]=[CH:47][C:42]([O:41][CH:38]([CH3:40])[CH3:39])=[CH:43][CH:44]=2)[C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:36])([F:37])[F:35])=[CH:30][N:29]=1)=[CH:23][CH:22]=2)=[O:18])[CH3:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Anhydrous CH2Cl2 (10 mL), followed by Et3N (92 μL, 0.66 mmol), pyridine (54 μL, 0.66 mmol) and 3 Å molecular sieves (1 g) were added to a mixture of 5-(5-(trifluoromethyl)pyrid-2-yl)indole-2-carboxylic acid ethyl ester (110 mg, 1.33 mmol; see step (b)), Cu(OAc)2 (120 mg, 0.66 mmol), and 4-isopropoxyphenylboronic acid (119 mg, 0.66 mmol). The mixture was stirred vigorously at ambient temperature for 18 h after which additional Cu(OAc)2 (59.9 mg, 0.33 mmol), 4-isopropoxyphenylboronic acid (59.4 mg, 0.33 mmol), Et3N (46.4 μL, 0.33 mmol) and pyridine (27 μL, 0.33 mmol) were added. After a further 30 h of stirring, the mixture was filtered through Celite®. The filter cake was washed with EtOAc and the solvents concentrated and purified by chromatography to give the sub-title compound.
Workup
- additionwere added
- filtrationthe mixture was filtered through Celite®
- washThe filter cake was washed with EtOAc
- concentrationthe solvents concentrated
- custompurified by chromatography
Sources & evidence
- ORD record
- ord-483deaccf5da4e09af80aa2847ef220f
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07705023B2
Reaction notes
Loading…