t-Butyl bromide → 3-tert-butyl-6-nitro-5-(trifluoromethyl)-1H-indole

Temperature

120 °C

A microwave vial charged with 6-nitro-5-(trifluoromethyl)-1H-indole (100 mg, 0.43 mmol), t-butyl bromide (30 mg, 0.22 mmol), zinc triflate (95 mg, 0.26 mmol), TBAI (80 mg, 0.22 mmol), DIEA (63 mg, 0.49 mmol) and toluene (1 mL) was sealed and heated in the microwave for 10 minutes at 120° C. The reaction mixture was quenched with water, the layers separated and the aqueous layer was extracted with DCM. The combined organic layer was dried over Na2SO4, filtered and concentrated. It was then purified by silica gel column chromatography using 0 to 20% EtOAc in hexanes to obtain 3-tert-butyl-6-nitro-5-(trifluoromethyl)-1H-indole. 1H NMR (400.0 MHz, CDCl3) δ 8.25 (s, 1H), 8.10 (s, 1H), 7.33 (d, J=2.5 Hz, 1H), 7.28 (s, 1H) and 1.50 (s, 9H) ppm.

1. customwas sealed
2. customThe reaction mixture was quenched with water
3. customthe layers separated
4. extractionthe aqueous layer was extracted with DCM
5. dry with materialThe combined organic layer was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customIt was then purified by silica gel column chromatography

ORD record

ord-a1369d3ccf764c4090304a6d2ee9584f

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354427B2