| 93% |
With sodium cyanoborohydride; acetic acid at 0 - 20℃; for 1h; |
14.A
EXAMPLE 14; Preparation of Methyl [(2l )- l - {(2lS}-2-[5-(4-{2-[(2S)-l - {(2S)-2-[(methoxycarbonyl)amino]-3- methyl butanoyl}pyrrolidin-2-yl]- l H-imidazol-5-yl}-l ,2-dihydropyrrolo[3,2, l -/:/]phenoxazin-9- yl)-l H-imidazol-2-yl]pyrrolidin-l-yl}-3-methyl- l -oxobutan-2-yl] carbamate (Compound 6); To a 0 °C solution of 7-methoxyindole (50 g; 0.34 mol) in AcOH (200 mL) was added NaBH3CN (17.92 g; 0.51 mol) at a rate to keep the reaction temperature below 5 °C. The reaction mixture was then stirred for 1 hour at room temperature, water (0.4 mL) was added, and the resulting solution was concentrated in vacuo. The residue obtained was diluted to 200 mL with EtOAc and the resulting solution was washed with 5% NaHC03, brine, dried over anhydrous Na2S04, filtered and concentrated in vacuo to provide compound Int-14a (47 g, 93%). MS (ESI) m/z (M+H)+: 149. |
| 93% |
With sodium cyanoborohydride In acetic acid at 0 - 20℃; for 1h; |
14.A
Synthesis of Com ound Int-14aInt 14aTo a 0 °C solution of 7-methoxyindole (50 g; 0.34 mol) in AcOH (200 mL) was added NaBH3CN (17.92 g; 0.51 mol) at a rate to keep the reaction temperature below 5 °C. The reaction mixture was then stirred for 1 hour at room temperature, water (0.4 mL) was added, and the resulting solution was concentrated in vacuo. The residue obtained was diluted to 200 mL with EtOAc and the resulting solution was washed with 5% NaHC03, brine, dried over anhydrous Na2S04, filtered and concentrated in vacuo to provide compound Int-14a (47 g, 93%) MS (ESI) m/z (M+H)+: 149. |
| 66% |
With sodium cyanoborohydride; acetic acid at 10℃; for 4h; |
6 Syntheses for Substituted Indoline Compounds
General procedure: The indole compound (2 mmol) was dissolved in acetic acid (20 mL). NaBH3CN (627 mg, 10 mmol) was added to the solution mixture portionwise at 10° C. The solution mixture was then stirred at 10° C. for 4 h, and then water was added to quench the reaction. Any organic volatile was removed by evaporation under reduced pressure, and the aqueous layer was extracted with dichloromethane. The dichloromethane layer was washed by dilute NaOH solution and then saturated NaCl solution, dried by MgSO4 and filtered. Volatile organic solvent was evaporated under reduced pressure, and the crude product was purified by column chromatography on silica gel using hexane/ethyl acetate (10:1, v/v) as eluent, yielding the indoline compound. Yield=66%. 1H NMR (CDCl3, 400 MHz): δ=6.87-6.91 (1H, m), 6.80 (1H, t, J=8.0 Hz), 6.72-6.76 (1H, m), 3.89-3.91 (1H, br), 3.89 (3H, s), 3.63 (2H, t, J=8.4 Hz), 3.13 (2H, t, J=8.4 Hz). 13C{1H} NMR (CDCl3, 100 MHz) δ=145.3, 140.5, 130.1, 119.0, 117.0, 109.0, 55.1, 47.5, 30.3. |
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
HazMat Fee +
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
