Potassium Carbonate → HCID 60004133, compound
Reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].Br[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.CCOC(C)=O>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:11]=1)[CH3:9])([CH3:2])([CH3:3])[CH3:4]Participants
6
Conditions
- Temperature
- 115 °C
Procedure
A mixture of (S)-[1-(3-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (10 g, 42.1 mmol), 3-bromopyridine (8 g, 50.6 mmol), potassium carbonate (powder, 14 g, 101 mmol) and copper iodide (325 mesh powder, 6 g, 31.6 mmol) was heated at 115° C. for 48 h. The reaction mixture was cooled to room temperature and concentrated in vacuo then CH2Cl2 (100 mL) was added, the reaction mixture was filtered, and the filtrate was washed with H2O (3×50 mL) and brine (100 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 2:1/Hexane:EtOAc to give the title product (6.4 g, 48% yield).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- concentrationconcentrated in vacuo
- additionCH2Cl2 (100 mL) was added
- filtrationthe reaction mixture was filtered
- washthe filtrate was washed with H2O (3×50 mL) and brine (100 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by flash column chromatography on silica gel eluting with 2:1/Hexane
Sources & evidence
- ORD record
- ord-93b345e0387c450785ecfdd91eb510f3
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900210B2
Reaction notes
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