Reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]2.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[CH:15]=[CH2:16].CCN(CC)CC.C(#N)C>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2].CCOC(C)=O>[CH2:19]([O:18][C:14](/[CH:15]=[CH:16]/[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]2)=[O:17])[CH3:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
5-Bromoindole-2-carboxylic acid (400 mg, 1.66 mmol) and tri-O-tolyl phosphine (96 mg, 0.32 mmol) were added to a microwave tube. Ethyl acrylate (0.56 ml, 5.6 mmol), Et3N (0.92 ml, 6.6 mmol), acetonitrile (2.5 ml) and Pd(OAc)2 (40 mg, 0.18 mmol) were added. The reaction was placed in a CEM microwave at 150 W, 90° C. for 30 minutes with 5 min ramp time. EtOAc was added and the reaction mixture filtered through celite. The celite pad was washed with DCM and the combined organic fractions removed to give a yellow solid. The solid was redissolved in DCM and extracted into saturated sodium hydrogen carbonate. The aqueous layer was washed with DCM and diethyl ether. The aqueous basic layer was acidified with 2M HCl (pH=5) and the product extracted into EtOAc. The solvent was removed to give the required product (370 mg, 86% yield). LCMS purity 86%, m/z 260 [M++H]+
Workup
- filtrationthe reaction mixture filtered through celite
- washThe celite pad was washed with DCM
- customthe combined organic fractions removed
- customto give a yellow solid
- extractionextracted into saturated sodium hydrogen carbonate
- washThe aqueous layer was washed with DCM and diethyl ether
- extractionthe product extracted into EtOAc
- customThe solvent was removed
Sources & evidence
- ORD record
- ord-fd9ad452f293436b86cd1c8eef150f25
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07939666B2
Linked notes
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