Potassium Carbonate → 3-Ethyl-2-isopropenyl-5-methyl-1H-indole

Temperature

110 °C

A 100 ml reaction flask equipped with a stirring bar and thermocouple are charged with Pd(OAc)2 (56 mg, 0.25 mmol), DtBPF (142 mg, 0.3 mmol), 2-chloro-4-methylaniline (0.71 g, 5 mmol), 2-methyl-1-hexen-3-yne (0.94 g, 10 mmol), K2CO3 (1.73 g, 12.5 mmol) and DMF (50 mL). The flask was purged with argon. The reaction was heated to 110° C. and stirred overnight. The reaction was complete after 20 h at 110° C. The mixture was filtered through a layer of diatomaceous earth and washed with EtOAc (10 mL). The filtrate was diluted with water (50 mL), extracted with EtOAc (100 mL×3). The combined organic phase was washed with water (50 mL×4) and brine, dried over MgSO4, filtered and concentrated to give a dark brown residue. The product was purified via chromatography on silica gel (hexane/EtOAc 50/1). The desired product was obtained as an off-white solid (0.6 g, 60%).

1. customA 100 ml reaction flask
2. customequipped with a stirring bar
3. customThe flask was purged with argon
4. waitThe reaction was complete after 20 h at 110° C
5. filtrationThe mixture was filtered through a layer of diatomaceous earth
6. washwashed with EtOAc (10 mL)
7. additionThe filtrate was diluted with water (50 mL)
8. extractionextracted with EtOAc (100 mL×3)
9. washThe combined organic phase was washed with water (50 mL×4) and brine
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated
13. customto give a dark brown residue
14. customThe product was purified via chromatography on silica gel (hexane/EtOAc 50/1)

ORD record

ord-44f29bcb6b1e45b091b926c9a364f39e

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07126009B2