Potassium Phosphate, Tribasic → 1-tert-Butyl 6-methyl 3-phenyl-1H-indole-1,6-dicarboxylate

A mixture of 1-tert-butyl 6-methyl 3-iodo-1H-indole-1,6-dicarboxylate 62a (5.02 mmol, 2.016 g), phenylboronic acid 1x (7.53 mmol, 0.92 g), Pd(OAc)2 (0.402 mmol, 90 mg), Sphos 0.904 mmol, (0.37 g), and K3PO4 (10.1 mmol, 2.13 g) in toluene (10 mL) in sealed reaction vial was stirred at room temperature for 2 min and then heated at 90° C. under N2 for 4 h. The reaction mixture was quenched with EtOAc and water. The organic layer was concentrated and purified by flash column chromatography (silica gel, 8% EtOAc/hexanes). The desired product was collected as a light yellow solid that was washed with small amount of hexanes to obtain 62b as a white solid.

1. customin sealed reaction vial
2. temperatureheated at 90° C. under N2 for 4 h
3. customThe reaction mixture was quenched with EtOAc and water
4. concentrationThe organic layer was concentrated
5. custompurified by flash column chromatography (silica gel, 8% EtOAc/hexanes)
6. customThe desired product was collected as a light yellow solid
7. washthat was washed with small amount of hexanes

ORD record

ord-f6ae86fe6c29430b873f84c105131411

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604017B2