Tri-o-tolylphosphine → 2-[3-(2-Fluoropyridin-4-yl)benzyl]pyrazolo[1,5-a]quinazolin-5(4h)-one
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][C:6]1[CH:19]=[C:9]2[NH:10][C:11](=[O:18])[C:12]3[C:17]([N:8]2[N:7]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3.[F:23][C:24]1[CH:29]=[C:28]([Sn](CCCC)(CCCC)CCCC)[CH:27]=[CH:26][N:25]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:23][C:24]1[CH:29]=[C:28]([C:2]2[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=2)[CH2:5][C:6]2[CH:19]=[C:9]3[NH:10][C:11](=[O:18])[C:12]4[C:17]([N:8]3[N:7]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:27]=[CH:26][N:25]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
A mixture of Example 61B (0.1 g, 0.282 mmol), 2-fluoro-4-(tributylstannyl)pyridine (0.11 g, 0.285 mmol) triethylamine (0.11 g, 1.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.039 g, 0.01 mmol) and tri-o-tolylphosphine (0.007 g, 0.023 mmol) in DMF (2 mL) was heated at 100° C. for 6 hr. The mixture was diluted with EtOAc and washed with sat NaHCO3, H2O and brine, then evaporated. The residue was purified by chromatography on silica gel with 20% to 80% ethylacetate in hexane to provide the desired product. 1H NMR (500 MHz, DMSO-d6) δ ppm 4.10 (s, 2 H) 5.75 (s, 1 H) 7.44-7.53 (m, 4 H) 7.68-7.74 (m, 2 H) 7.83-7.88 (m, 2 H) 8.04 (d, J=8.24 Hz, 1 H) 8.11 (d, J=6.71 Hz, 1 H) 8.30 (d, J=5.49 Hz, 1 H).
Workup
- washwashed
- customevaporated
- customThe residue was purified by chromatography on silica gel with 20% to 80% ethylacetate in hexane
Sources & evidence
- ORD record
- ord-6af189e2b25744bb99e73e3ccca36c11
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08183250B2
Reaction notes
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