Toluene → HCID 71289517, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1 (60 mg, 0.12 mmol) in THF:toluene (10 mL, 1:1) were added 4-bromo-2,6-dimethylpyridine (22 mg, 0.12 mmol) and CsF (54 mg, 0.36 mmol) at RT under inert atmosphere and degassed for 15 min in argon atmosphere. To the resulting solution was added Pd(dppf)2Cl2 (8.0 mg, 0.012 mmol) at RT and again degassed for another 10 min. The resulting reaction mixture was heated to 80° C. and stirred for 12 h; progress of the reaction was monitored by TLC. The reaction mixture was allowed to cool to RT and concentrated under reduced pressure to obtain the crude. The crude material was purified by silica gel column chromatography (eluent: 5% MeOH/CH2Cl2) to afford the title compound 92 (6.0 mg, 10.16%) as yellow solid. 1H NMR (500 MHz, DMSO-d6): δ 10.50 (bs, 1H), 9.64 (bs, 1H), 8.78 (bs, 1H), 8.31 (s, 1H), 8.09 (d, J=8.0 Hz, 1H), 7.88 (d, J=7.5 Hz, 1H), 7.63 (t, J=8.0 Hz, 1H), 7.42 (s, 2H), 7.38-7.31 (m, 3H), 7.25-7.23 (m, 5H), 6.64 (t, J=6.0 Hz, 1H), 4.31 (d, J=6.0 Hz, 2H), 3.56 (s, 2H), 2.49 (s, 6H). LCMS: m/z 490 [M+1]+

Provenance & Evidence