Cesium carbonate → HCID 66728944, compound
Reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[CH3:9][C:10]1(C)[C:14](C)(C)OB(C(C)=C)O1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O.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>[CH2:9]=[C:10]([C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1)[CH3:14]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
5-Bromopyridin-3-amine (0.433 g, 2.5 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (0.630 g, 3.75 mmol), Cs2CO3 (3.10 g, 9.5 mmol) and Pd(PPh3)4 (0.289 g, 0.25 mmol) were suspended in DMF/H2O (3:1, 20 mL). The reaction mixture was degassed with N2 and heated at 90° C. for 16 h. Solvent was removed under reduced pressure. The residue was diluted with H2O (20 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine (20 mL), dried, concentrated in vacuo and purified by chromatography to afford 5-(prop-1-en-2-yl)pyridin-3-amine (0.773 g, 230%) as a dark yellow oil. MS (ESI) m/z: 135.0 (M+H+).
Workup
- customThe reaction mixture was degassed with N2
- customSolvent was removed under reduced pressure
- additionThe residue was diluted with H2O (20 mL)
- extractionextracted with EtOAc (3×50 mL)
- washThe combined organic layers were washed with brine (20 mL)
- customdried
- concentrationconcentrated in vacuo
- custompurified by chromatography
Sources & evidence
- ORD record
- ord-e2135403269942138b98950d528ebe2b
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143293B2
Reaction notes
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