Phosphorus tribromide → 6-[(1-Methylethyl)-2-propen-1-ylamino]-3-pyridinecarbonitrile
Reaction equation
P(Br)(Br)[Br:2].O[CH:6]([C:8]1[O:9][C:10](=[O:31])[C:11]2[C:16]([C:17]=1[C:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:7].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:2][CH:6]([C:8]1[O:9][C:10](=[O:31])[C:11]2[C:16]([C:17]=1[C:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:7]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
1M PBr3 (0.36 ml, 0.363 mmol) in DCM was added drop-wise to a solution of tert-butyl 4-(3-(1-hydroxyethyl)-1-oxo-1H-isochromen-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate (intermediate B12, 135 mg, 0.363 mmol) in DCM (5 ml). Reaction mixture was then dried under reduced pressure and dissolved in DCM (5 ml). Di-tert-butyl dicarbonate (0.34 ml, 1.454 mmol) and DMAP (89 mg, 0.727 mmol) were added simultaneously, and the mixture stirred overnight at RT. Reaction mixture was straightforward purified on Biotage SNAP 50 g silica cartridge with a gradient of hexane and EtOAc give the title compound (100 mg, 63.3%) as a yellowish oil.
Workup
- customReaction mixture
- customwas then dried under reduced pressure
- dissolutiondissolved in DCM (5 ml)
- customReaction mixture
- customwas straightforward purified on Biotage SNAP 50 g silica cartridge with a gradient of hexane and EtOAc
Sources & evidence
- ORD record
- ord-c1c04b59e86a42e2b320851d7fe8013a
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321776B2
Reaction notes
Loading…