2-Methyl-6-(tributylstannyl)pyridine → 2-((S)-1-(8-Chloro-2-(6-methylpyridin-2-yl)quinolin-3-yl)ethyl)isoindoline-1,3-dione
Reaction equation
Cl[C:2]1[C:11]([C@@H:12]([N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])[CH3:13])=[CH:10][C:9]2[C:4](=[C:5]([Cl:25])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Sn](CCCC)(CCCC)CCCC)[N:28]=1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:25][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:29]1[CH:30]=[CH:31][CH:32]=[C:27]([CH3:26])[N:28]=1)[C:11]([C@@H:12]([N:14]1[C:15](=[O:24])[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]1=[O:23])[CH3:13])=[CH:10]2Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
A stirred mixture of (S)-2-(1-(2,8-dichloroquinolin-3-yl)ethyl)isoindoline-1,3-dione (254.3 mg, 0.685 mmol) and tetrakis(triphenylphosphine)palladium (79.16 mg, 68.50 μmol), 2-methyl-6-(tributylstannyl)pyridine (523.6 mg, 1.37 mmol) in dioxane (degassed) was heated at 100° C. for 28 h, complete by LC-MS solvent removed and chromatographed: 89:9:1 (DCM/MeOH,NH4OH)gradient. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.78 (1H, s), 8.15 (1H, dd, J=8.3, 1.3 Hz), 7.98 (1H, dd, J=7.5, 1.3 Hz), 7.73-7.78 (2H, m), 7.58-7.69 (4H, m), 7.36 (1H, d, J=7.6 Hz), 7.16 (1H, d, J=7.6 Hz), 6.11-6.19 (1H, m), 2.33 (3H, s), 1.82 (3H, d, J=7.0 Hz)
Workup
- customremoved
- customchromatographed
Sources & evidence
- ORD record
- ord-da31433ef15343fc94fda53689340b9d
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193199B2
Reaction notes
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