2-Bromopyridine → HCID 59837383, compound

Participants

Reaction Conditions

Reaction Steps

C-{4-[4-(3-[1,4]Oxazepan-4-yl-propoxy)-phenyl]-tetrahydro-pyran-4-yl}-methylamine (210 mg, 0.48 mmol) was added to a solution of 2-bromopyridine (70 mg, 0.42 mmol), Pd2(dba)3 (91 mg, 0.1 mmol), BINAP (126 mg, 2 mmol) and sodium tert-butoxide (56 mg, 5.7 mmol) in toluene (3 ml). This solution was heated in the microwave (Smith Personal Synthesiser) at 110° C. for 15 minutes. The solution was filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified by column chromatography, eluting with a gradient of DCM:MeOH:NH3 (from 99:1:0.1 to 95:5:0.5) to afford the title compound as a yellow oil (120 mg, 59%). 1H NMR (400 MHz, CD3OD) δ 1.88-2.00 (m, 6H), 2.17 (m, 2H), 2.68-2.79 (m, 6H), 3.43 (s, 2H), 3.50 (m, 2H), 3.76 (m, 2H), 3.80 (m, 4H), 4.03 (t, 2H), 6.39 (d, 1H), 6.44 (t, 1H), 6.91 (d, 2H), 7.33 (m, 3H), 7.81 (d, 1H). HRMS ESI+ m/z 426.2741 [MH]+.

Provenance & Evidence