Potassium Carbonate → HCID 68617973, compound
Reaction equation
Br[C:2]1[C:3]([F:14])=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2.[C:15]1(/[CH:21]=[CH:22]/B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>>[F:14][C:3]1[C:2](/[CH:22]=[CH:21]/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([O:12][CH3:13])=[N:10]2)=[N:5][CH:4]=1Participants
4
Procedure
8-bromo-7-fluoro-2-methoxy-[1,5]naphthyridine (prepared as in WO 2004/058144; 7 g, 27.2 mmol), trans-phenylvinyl boronic acid (4.23 g, 1.05 eq) and K2CO3 (4.9 g) were introduced in a two-necked flask. The atmosphere was flushed with nitrogen and dioxane (40 ml) and water (10 ml) were added. The mixture was stirred at rt for 5 min and Pd(PPh3)4 (1.56 g, 5 mol %) was added. The mixture was heated at reflux overnight. After cooling, the solvent was evaporated in vacuo and the residue was extracted with EA (2×150 ml). The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was chromatographed (Hept-EA 2-1) to afford the title compound (7.2 g, 94% yield) as a white solid.
Workup
- customThe atmosphere was flushed with nitrogen and dioxane (40 ml) and water (10 ml)
- additionwere added
- additionPd(PPh3)4 (1.56 g, 5 mol %) was added
- temperatureThe mixture was heated
- temperatureat reflux overnight
- temperatureAfter cooling
- customthe solvent was evaporated in vacuo
- extractionthe residue was extracted with EA (2×150 ml)
- washThe combined extracts were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated to dryness
- customThe residue was chromatographed (Hept-EA 2-1)
Sources & evidence
- ORD record
- ord-963d3809dd1f4126bb04c67597be8e2f
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820655B2
Reaction notes
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