Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([S:23][CH3:24])=[N:19][NH:20]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.CCOC(C)=O>C(Cl)Cl.CCCCCCC.CC([O-])=O.CC([O-])=O.[Cu+2]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([S:23][CH3:24])=[N:19][N:20]3[C:30]3[CH:31]=[C:26]([CH3:25])[CH:27]=[CH:28][CH:29]=3)=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a mixture of 4-(3-methylsulfanyl-1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (63 mg, 0.18 mmol) and 3-methyl phenyl boronic acid (50 mg, 0.36 mmol) in CH2Cl2 (1.5 mL) were added TEA (0.051 mL, 0.36 mmol) and Cu(OAc)2 (33 mg, 0.18 mmol). The resulting mixture was stirred at room temperature for 16 h. The resulting mixture was loaded onto a silica-gel column and chromatography (gradient eluent heptane to 50% EtOAc in heptane) to yield 4-(3-Methylsulfanyl-1-m-tolyl-1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as colorless film stuck on flask wall.
Sources & evidence
- ORD record
- ord-345061ce8fc3497e974a688b5499a2a0
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822447B2
Linked notes
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