反应详情

A round-bottomed flask was charged with 2-bromo-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (150 mg, 0.40 mmol), HOBT (68 mg, 0.44 mmol) and EDC (85 mg, 0.44 mmol). DMF (1.8 ml) was added followed by (S)-3,3-dimethylbutan-2-amine (0.10 ml, 0.73 mmol) and N,N-diisopropylethylamine (0.11 ml, 0.63 mmol). The reaction mixture was stirred at room temperature overnight then quenched with water and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then combined, dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-20% EtOAc) to afford 97 mg (50%) of 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-1,2,2-trimethyl-propyl)-amide as a light brown oil.

1. customthen quenched with water
2. extractionextracted with diethyl ether (2×)
3. washThe combined organic layers were washed twice with water and once with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-20% EtOAc)