1,4-Dioxane → HCID 23651430, compound

Participants

Reaction Conditions

Reaction Steps

Pd2(dba)3 (0.5 mol %, 5.175 mg), ligand 12-(dicyclohexylphosphino)-2′ (N,N-dimethylamino) biphenyl (7.86 mg, 20 mol %), and sodium tert-butoxide (13.45 mg, 0.14 mmol) were weighed in air and transferred into a microwave tube. 5-fluoro-N,N-dimethyl-1′-(piperidin-4-yl)spiro[indoline-3,4′-piperidine]-1-carboxamide 4ba (36.0 mg, 0.1 mmol) and 2-iodo pyrazine (20.5 mg, 0.1 μmol) and 1 mL of dioxane were added. The tube was purged with N2 and stirred at 80° C. for 16 hours. The reaction was diluted with methanol, filtered (Whatman 0.2 μm PTFE) and subjected to reverse-phase HPLC purification [2-50% CH3CN gradient over 13 min with 0.1% TFA (aq), 35 mL/min, 1.5 mL injected] to provide compound no. 52. 1H NMR (400 MHz, MeOD) 8.63 (d, J=2.6 Hz, 1H), 8.52 (s, 1H), 7.92 (d, J=3.0 Hz, 1H), 7.28-7.23 (m, 2H), 7.03-6.98 (m, 2H), 4.75-7.72 (m, 2H), 3.93 (s, 2H), 3.70-3.78 (m, 3H), 3.33-3.18 (m, 4H), 3.00 (s, 6H), 2.42-2.35 (m, 4H), 2.05-1.92 (m, 4H). LC/MS (10-99% CH3CN/0.05% TFA gradient over 5 min): m/z 421.1, retention time 2.03 minutes.

Provenance & Evidence