5-(2-Bromopyrid-5-yl)-1-azabicyclo[3.2.1]oct-3-ene → 5-[2-(-1-Triphenylmethylimidazol-4-yl)pyrid-5-yl]-1-azabicyclo[3.2.1]oct-3-ene
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:15][N:12]([CH2:13][CH2:14]2)[CH2:11][CH:10]=[CH:9]3)=[CH:4][N:3]=1.[C:16]1([C:22]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:23]2[CH:27]=[C:26]([Sn](CCCC)(CCCC)CCCC)[N:25]=[CH:24]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1.C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:47]1([C:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[N:23]2[CH:27]=[C:26]([C:2]3[CH:7]=[CH:6][C:5]([C:8]45[CH2:15][N:12]([CH2:13][CH2:14]4)[CH2:11][CH:10]=[CH:9]5)=[CH:4][N:3]=3)[N:25]=[CH:24]2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 85 °C
Procedure
0.25 g (0.94 mmol) of 5-(2-bromopyrid-5-yl)-1-azabicyclo[3.2.1]oct-3-ene (WO 03/057 697) dissolved in 3 ml of tetrahydrofuran, 1.24 g (2.07 mmol) of 1-triphenylmethyl-4-tributylstannylimidazole and 0.06 g (0.08 mmol) of bis(triphenylphosphine)dichloropalladium are successively introduced into a 10 ml three-necked round-bottomed flask. The mixture is then heated at 85° C. for 15 hours and then diluted in 10 ml of chloroform and 10 ml of saturated aqueous sodium carbonate solution.
Sources & evidence
- ORD record
- ord-d9bf7d10ce614b92ba8fb816d151f51e
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541440B2
Reaction notes
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