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5-(6-fluoro-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 100.0℃; for 0.08333330000000001h;Microwave irradiation;
A mixture of 5-bromo-N-methylpyridin-2-amine (50 mg, 0.27 mmol), bis(pinacolato)diboron (75 mg, 0.30 mmol), Pd(dprhof)Cl2*DCM (6.5 mg, 0.008 mmol) and S KOAc (79 mg, 0.80 mmol) in DMF (2 mL) was heated at 150 C for 10 minutes in a microwave reactor. Then 2-bromo-6-fluoro-l,3-benzothiazole (93 mg, 0.40 mmol), another batch of Pd(dppf)Cl2*DCM (6.5 mg, 0.008 mmol) and 2 M aq. K2CO3 (0.5 mL) were added and the reaction mixture was heated at 100 C for 5 minutes in a microwave reactor. The mixture was allowed to cool and was partitioned between EtOAc and H2O. The 0 organic phase was washed with water and brine and was dried (Na2SO4). Concentration <n="94"/>under vacuum and purification by HPLC gave the title compound (8 mg). 1H NMR (CHLOROFORM-c/: CD3OD) delta 8.61 (d, 1 H) 8.02 (dd, 1 H) 7.87 (dd, 1 H) 7.57 (dd, 1 H) 7.22-7.15 (m, 1 H) 6.55 (d, 1 H) 2.94 (s, 3 H); MS m/z (M+H) 260, (M-H) 258.
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 150℃; for 0.166667h;Microwave irradiation;
A mixture of <strong>[84539-30-0]5-bromo-N-methylpyridin-2-amine</strong> (50 mg, 0.27 mmol), bis(pinacolato)diboron (75 mg, 0.30 mmol), Pd(dprhof)Cl2*DCM (6.5 mg, 0.008 mmol) and S KOAc (79 mg, 0.80 mmol) in DMF (2 mL) was heated at 150 C for 10 minutes in a microwave reactor. Then 2-bromo-6-fluoro-l,3-benzothiazole (93 mg, 0.40 mmol), another batch of Pd(dppf)Cl2*DCM (6.5 mg, 0.008 mmol) and 2 M aq. K2CO3 (0.5 mL) were added and the reaction mixture was heated at 100 C for 5 minutes in a microwave reactor. The mixture was allowed to cool and was partitioned between EtOAc and H2O. The 0 organic phase was washed with water and brine and was dried (Na2SO4). Concentration <n="94"/>under vacuum and purification by HPLC gave the title compound (8 mg). 1H NMR (CHLOROFORM-c/: CD3OD) delta 8.61 (d, 1 H) 8.02 (dd, 1 H) 7.87 (dd, 1 H) 7.57 (dd, 1 H) 7.22-7.15 (m, 1 H) 6.55 (d, 1 H) 2.94 (s, 3 H); MS m/z (M+H) 260, (M-H) 258.
With potassium acetate;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 80 - 90℃;
Example B-2: Preparation of (2S)-1-(4-(1-isopropyl-3-(6-(methylamino)pyridin-3-yl)-1H-pyrazol-4- yl)pyrimidin-2-ylamino)propan-2-ol (B-2)H2N N B-2-1 B-2-2 B-2-3B-2Preparation of N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2 -amine B-2-3B-2-2 B-2-3 <n="64"/>To a solution of <strong>[84539-30-0]5-bromo-N-methylpyridin-2-amine</strong> B-2-2 (1 g, 5.37 mmol) in DMF (30 mL) were added KOAc (1.58 g, 16.1 mmol) and bis(pinacolato)diboron (2 g, 8.06 mmol). The resulting mixture was degassed under N2 for 2 minutes. Then Pd(PPh3J2CI2 (0.5 g, 0.53 mmol) was added and the mixture was degassed again. The reaction was heated to 80-900C and stirred overnight. DMF was removed under reduced pressure. The residue was dissolved with EtOAc (40 mL), washed with saturated aqueous NaCI, dried over Na2SO4 and concentrated to give crude N-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)pyridin-2-amine B-2-3 (2.3 g), which was used directly in next step.
With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 20℃; for 16h;
ntermediate 8A-methyi-5-(4, -tetramethyi-1 ,3,2-dioxaborolan-2-yl)pyridin-2-ami ne[091 ] A mixture of 2-chloro-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine (200 mg, 0.84 mmol), methanamine (277 mg, 8.4 mmol), and DIPEA (0.35 ml_, 2.01 mmol) in dioxane (5 ml_) was stirred at room temperature for 16 hours. It was then concentrated under reduced pressure, and the residue was treated in EtOAc. The insoluble solid was removed by filtration, and the organic solution was concentrated under reduced pressure to give the title compound.
With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 20℃; for 16h;
A mixture of <strong>[444120-94-9]2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine</strong> (200 mg, 0.84 mmol), methanamine (277 mg, 8.4 mmol), and DIPEA (0.35 mL, 2.01 mmol) in dioxane (5 mL) was stirred at room temperature for 16 hours. It was then concentrated under reduced pressure, and the residue was treated in EtOAc. The insoluble solid was removed by filtration, and the organic solution was concentrated under reduced pressure to give the title compound.