Pyridine → N-{3-[4-(6-Fluoropyridin-3-yloxy)phenyl]-1-methylpropyl}acetamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][N:3]=1.C(N1C=CN=C1)CCC.[OH:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH:35]([NH:37][C:38](=[O:40])[CH3:39])[CH3:36])=[CH:29][CH:28]=1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[F:1][C:2]1[N:3]=[CH:4][C:5]([O:26][C:27]2[CH:28]=[CH:29][C:30]([CH2:33][CH2:34][CH:35]([NH:37][C:38](=[O:40])[CH3:39])[CH3:36])=[CH:31][CH:32]=2)=[CH:6][CH:7]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (900 mg, 4.03 mmol), anhydrous copper acetate (550 mg, 3.03 mmol), 1-butylimidazole (175 mg, 1.41 mmol), N-[3-(4-hydroxyphenyl)-1-methylpropyl]acetamide (418 mg, 2.02 mmol) and pyridine (0.326 ml, 4.03 mmol) were admixed with 25 ml of toluene, and stirred at 100° C. for 15 h, under argon. The reaction mixture was filtered and the filtrate was concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 394 mg (32%), M+H+: 303.0.
Workup
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate was concentrated
- custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)
Sources & evidence
- ORD record
- ord-ac2c312b1117453ba9b2827d4c5e0200
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470841B2
Reaction notes
Loading…