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General Procedure for the Microwave-Enhanced Suzuki Reaction and Cadogan Cyclization
- Synthesis of 8
H
-Thieno[2,3-
b
]indole (
4q): 3-Bromothiophene (2q, 0.041 g, 0.25 mmol), 2-nitrophenylboronic acid (0.054 g, 0.325 mmol), NaHCO3 (0.063 g, 0.75 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.015 g, 5 mol%)
were suspended in DMF (1.5 mL) and H2O (1.5 mL) in a 10 mL glass vial equipped with a small stirring magnet. The vial was
sealed tightly with an aluminium-Teflon® crimp top and the mixture was irradiated in the cavity of a mono-mode CEM®-Discover machine for 15 min at a pre-selected temperature of 150 °C, using a maximum
irradiation power of 100 W. After the reaction, the vial was cooled to 50 °C by gas
jet cooling. The crude mixture was partitioned between Et2O and H2O (25 mL each) and the aqueous layer was extracted with Et2O (3 × 20 mL). The combined organic layers were dried on MgSO4 and solvents were removed under vacuum to yield the crude product as yellow oil.
Column chromatography [silica gel, heptane-EtOAc (9:1)] afforded the biaryl compound
3q (0.046 g, 890%) as yellowish oily material.
The nitro compound 3q was suspended in triethyl phosphate (3 mL) in a tightly sealed 10 mL glass vial and
was irradiated at a maximum irradiation power of 300 W for 15 min at a pre-selected
temperature of 210 °C. After the reaction, the vial was cooled to 50 °C by gas jet
cooling and the contents were transferred to a 50 mL flask with the help of EtOAc
(10 mL). This mixture was then heated to 80 °C with an excess of HCl (6 N, 10 mL)
and maintained at the temperature for 3 h. After cooling to r.t., the mixture was
partitioned between H2O and EtOAc (20 mL each) and the aqueous layer was further extracted with EtOAc (3
× 10 mL). The combined organic layers were dried over MgSO4 and solvents were removed under reduced pressure, and further purification by column
chromatography (silica gel, heptane-EtOAc, 9:1) afforded the thieno-indole 4q (0.0296 g, 76%). 1H NMR (300 MHz, CDCl3): δ = 6.92 (d, 1 H, J = 5.2 Hz), 7.19-7.27 (m, 2 H), 7.36 (d, 1 H, J = 5.2 Hz), 7.41 (d, 1 H, J = 8.0 Hz), 7.81 (dd, 1 H, J = 7.6, 0.8 Hz), 8.22 (br s, 1 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 111.2, 117.1, 117.6, 119.3, 119.9, 122.2, 122.5, 125.6, 141.2, 142.2 ppm. DEPT-NMR
(75 MHz, CDCl3): δ = 111.2, 117.1, 117.6, 119.3, 122.5, 125.6 ppm. MS (EI): 173 [M+]. HRMS (EI): m/z calcd for C10H07NS [M+]: 173.02992; found: 173.02986.
