تفاعل #1590451

معادلة التفاعل

3-chloro-N-(3-ethynyl-adamantan-1-yl)-benzamide

2-chloro-6-methylpyrazine

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title compound

المردود 38.9%

3-Chloro-N-[3-(6-methyl-pyrazin-2-ylethynyl)-adamantan-1-yl]-benzamide

المردود 38.9%

المذيبات

ethyl acetate

triethylamine

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was cooled to room temperature
2. 2
   غسيلwashed with water (50 mL) and brine
3. 3
   تجفيفdried over Na2SO4
4. 4
   تركيزconcentrated under reduced pressure
5. 5
   أخرىThe resulting residue was purified by Prep HPLC

الإجراء التجريبي

To a stirred mixture of intermediate 8, 3-chloro-N-(3-ethynyl-adamantan-1-yl)-benzamide (60 mg, 0.19 mmol) and 2-chloro-6-methylpyrazine (60 mg, 0.47 mmol) in triethylamine (0.5 mL) and acetonitrile (2 mL) was added Pd(PPh3)4 (3 mg, 0.02 mmol), followed by an addition of CuI (3 mg, 0.016 mmol). After heated at 70° C. for three hours, the reaction mixture was cooled to room temperature, diluted with ethyl acetate (30 mL), washed with water (50 mL) and brine, dried over Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by Prep HPLC to give 30 mg (38%) of the title compound, 3-chloro-N-[3-(6-methyl-pyrazin-2-ylethynyl)-adamantan-1-yl]-benzamide. 1H NMR (500 MHz, CDCl3): δ 8.57 (brs, 1H), 7.69 (t, J=2.0 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.35 (t, J=8.0 Hz, 1H), 5.78 (s, 1H), 2.57 (s, 3H), 2.40 (s, 2H), 2.25 (s, 2H), 2.17-2.15 (m, 2H), 2.06-1.96 (m, 6H), 1.73-1.70 (m, 2H); ESI-MS m/z: 406 (M+H)+.

المصدر