HCID 46449, compound → HCID 58707347, compound

Participants

Reaction Steps

A solution of 1,2,3,4-tetrahydro-5,8-dimethoxynaphthalen-1-amine (1.1 g mL, 5.31 mmol), 2,4-difluoro-1-(methylsulfonyl)benzene (1.02 g, 5.31 mmol) and diisopropylethylamine (3.7 mL, 21.26 mmol) in N,N-dimethylformamide (10 mL) was stirred at 90° C. for 16 h. The reaction mixture was diluted with water and extracted with diethyl ether. The combined extracts were washed with water and brine, dried, and concentrated under reduced pressure to yield 1.95 g of a yellow oil. The residue was purified by PTLC (25% ethyl acetate in hexanes) to give 1.26 g (63%) of the desired aniline: 1H NMR (400 MHz, CDCl3) δ 7.40 (dd, 1H), 6.73 (d, 1H), 6.66 (m, 2H), 6.44 (dt, 1H), 6.22 (br d, 1H), 4.79 (br s, 1H), 3.80 (s, 3H), 3.67 (s, 3H), 2.96-2.88 (m, 4H), 2.46-2.37 (m, 1H), 2.17-2.12 (br d, 1H), 1.92-1.84 (m, 1H), 1.78-1.60 (m, 2H). MS (ESI) m/z: Calculated: 379.13; Observed: 402.2 (M++23).

Provenance & Evidence