N-Methylethylamine → HCID 136375863, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[5-(2-chloro-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenol (549 mg, 1.74 mmol) and Na tert.-butylate (346 mg, 3.60 mmol) in ethyl-methylamine (10 mL), Xantphos (106 mg, 0.18 mmol) and Pd(OAc)2 (47 mg, 0.21 mmol) is added. The mixture is stirred in an autoclave at 80° C. for 24 h. The dark mixture is cooled to rt, diluted with EA (200 mL), washed three times with sat. aq. NaHCO3-solution, dried over MgSO4, filtered and concentrated. The crude product is purified by MPLC on silica gel eluting with EA containing 20% of methanol to give 4-{5-[2-(ethyl-methyl-amino)-6-methyl-pyridin-4-yl]-[1,2,4]oxadiazol-3-yl}-2,6-dimethyl-phenol (119 mg) as a yellow solid; LC-MS: tR=0.83 min; [M+1]+=339.10; 1H NMR (D6-DMSO): δ 1.12 (m, 3H), 2.26 (s, 6H), 2.43 (s, 3H), 2.88-2.98 (m, 2H), 3.07 (s, 3H), 7.00 (s, 1H), 7.08 (s, 1H), 7.67 (s br, 1H), 7.68 (s, 1H), 8.94 (s br, 1H).

Provenance & Evidence