Tributylvinyltin → HCID 11609093, compound
Reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][C:12]([CH3:16])([CH3:15])[CH2:13][N:14]=[C:6]3[C:5]3([O:21][CH2:20][CH2:19][CH2:18][O:17]3)[C:4]=2[CH:3]=1.[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]CC>O1CCOCC1>[CH3:15][C:12]1([CH3:16])[CH2:11][N:7]2[C:8]3[CH:9]=[CH:10][C:2]([CH:22]=[CH2:23])=[CH:3][C:4]=3[C:5]3([O:17][CH2:18][CH2:19][CH2:20][O:21]3)[C:6]2=[N:14][CH2:13]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To the stirred solution of 8′-bromo-3′,3′-dimethyl-3′,4′-dihydro-2′H-spiro[1,3-dioxane-2,10′-pyrimido[1,2- a]indole](2.576 g, 7.330 mmol) in dioxane (70 mL) was added tributyl (vinyl) tin (3.490 g, 10.995 mmol) and the solution was degassed with N2 for 15 min. Pd(PPh3) 4 was added and the mixture was stirred at 100° C. for 6 hr. The reaction was diluted with EtOAc, washed with brine and concentrated. The resulting residue was dissolved in EtOAc and stirred with 1M KF solution (20 mL) overnight. The reaction was filtered and the filtrate was washed with brine. The organics were dried over Na2SO4 and concentrated to give the title compound as white solid (1.720 g, 79%). NMR (400 Mz, DMSO-d6): consistent.
Workup
- customthe solution was degassed with N2 for 15 min
- additionPd(PPh3) 4 was added
- additionThe reaction was diluted with EtOAc
- washwashed with brine
- concentrationconcentrated
- dissolutionThe resulting residue was dissolved in EtOAc
- stirringstirred with 1M KF solution (20 mL) overnight
- filtrationThe reaction was filtered
- washthe filtrate was washed with brine
- dry with materialThe organics were dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6e42d3be323a428a8a0e3abf117cbe39
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07256198B2
Reaction notes
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