Cesium fluoride → HCID 86700856, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]12[CH2:12][CH2:11][C:8]([C:13]3[CH:18]=[CH:17][C:16](Cl)=[CH:15][CH:14]=3)([CH2:9][CH2:10]1)[O:7][CH2:6]2.[C:21]([C:25]1[O:29][C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34](B3OC(C)(C)C(C)(C)O3)=[CH:33][CH:32]=2)=[N:27][N:26]=1)([CH3:24])([CH3:23])[CH3:22].[F-].[Cs+]>O1CCOCC1.O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]12[CH2:12][CH2:11][C:8]([C:13]3[CH:18]=[CH:17][C:16]([C:34]4[CH:33]=[CH:32][C:31]([NH:30][C:28]5[O:29][C:25]([C:21]([CH3:24])([CH3:23])[CH3:22])=[N:26][N:27]=5)=[CH:36][CH:35]=4)=[CH:15][CH:14]=3)([CH2:9][CH2:10]1)[O:7][CH2:6]2Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
To a solution of [1-(4-chloro-phenyl)-2-oxa-bicyclo[2.2.2]oct-4-yl]-acetic acid methyl ester (0.29 g, 0.984 mmol) and (5-tert-butyl-[1,3,4]oxadiazol-2-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine (0.338 g, 0.984 mmol) in dioxane (8 ml) and water (0.8 ml), was added caesium fluoride (0.448 g, 2.95 mmol) and Pd(amphos)Cl2 (0.070 g, 0.098 mmol). The mixture was flushed with nitrogen for three times and heated at 90° C. for 16 hours. The reaction mixture was filtered, and the solid was washed with water (10 ml) and ethyl acetate (3 ml) to afford crude {1-[4′-(5-tert-butyl-[1,3,4]oxadiazol-2-ylamino)-biphenyl-4-yl]-2-oxa-bicyclo[2.2.2]oct-4-yl}-acetic acid methyl ester (0.27 g, 58%) as white solid. [MS+1] 476.31.
Workup
- customThe mixture was flushed with nitrogen for three times
- filtrationThe reaction mixture was filtered
- washthe solid was washed with water (10 ml) and ethyl acetate (3 ml)
Sources & evidence
- ORD record
- ord-e6b946e0cf4145bd96bd7488cbf3ba77
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993619B2
Reaction notes
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