Water → Butyl (2E)-3-[2-{(2,2-dimethylpropanoyl)[(2-oxo-1,3-dioxolan-4-yl)methyl]amino}-6-(methyloxy)-3-pyridinyl]-2-propenoate
Reaction equation
Br[C:2]1[C:3]([N:10]([CH2:17][CH:18]2[CH2:22][O:21][C:20](=[O:23])[O:19]2)[C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[C:24]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:27])[CH:25]=[CH2:26].O>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:13][C:12]([CH3:15])([CH3:14])[C:11]([N:10]([CH2:17][CH:18]1[CH2:22][O:21][C:20](=[O:23])[O:19]1)[C:3]1[C:2](/[CH:26]=[CH:25]/[C:24]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27])=[CH:7][CH:6]=[C:5]([O:8][CH3:9])[N:4]=1)=[O:16]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
A mixture of N-[3-bromo-6-(methyloxy)-2-pyridinyl]-2,2-dimethyl-N-[(2-oxo-1,3-dioxolan-4-yl)methyl]propanamide (5.722 g, 14.722 mmol), Pd(PtBu3)2 (151 mg, 0.296 mmol), Pd2(dba)3 (135 mg, 0.149 mmol), in 1,4-dioxane (40 ml) was treated with N,N′-dicyclohexylmethylamine (3.48 ml, 16.265 mmol) and n-butyl acrylate (2.54 ml, 17.743 mmol) and the mixture was then heated at 80° C. for 1 h. The reaction was then cooled, treated with water (200 ml), extracted with DCM (3×200 ml). The organic extracts were dried (MgSO4), and evaporated and chromatographed (0-50% ethyl acetate:Hexane) to give the product as a yellow oil (6.156 g, 96%).
Workup
- temperatureThe reaction was then cooled
- extractionextracted with DCM (3×200 ml)
- dry with materialThe organic extracts were dried (MgSO4)
- customevaporated
- customchromatographed (0-50% ethyl acetate:Hexane)
Sources & evidence
- ORD record
- ord-9dfaf396827f484e8d0d6eb6e70285af
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389524B2
Reaction notes
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