6'-Bromo-1',2'-dihydrospiro[cyclohexane-1,3'-indole]-2'-one synthesis
- Product Name:6'-Bromo-1',2'-dihydrospiro[cyclohexane-1,3'-indole]-2'-one
- CAS Number:1190866-02-4
- Molecular formula:C13H14BrNO
- Molecular Weight:280.16
Yield: 60.6%
Reaction Conditions:
Stage #1:6-bromo-2,3-dihydro-1H-indole-2-one with lithium hexamethyldisilazane in tetrahydrofuran at -78; for 0.5 h;Inert atmosphere;
Stage #2:1,5-dibromo-pentane in tetrahydrofuran at -78 - 20; for 12.5 h;
Steps:
4.1 Step 1: Synthesis of 6’-Bromospiro[cyclohexane-1,3’-indolin]-2’-one (15)
To a stirred solution of compound 14 (3 g, 14.15 mmol) in dry THF (30 mL) at -78°C under argon atmosphere, LiHMDS (1M in THF, 42 mL, 42.45 mmol) was added drop wise and stirred at same temperature for 30 mm. To this solution, 1, 5 -dibromopentane (1.91 mL,14.15 mmol) was added at -78 °C and stirred for another 30 mm. The resulting reaction was stirred at RT for 12 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was quenched with sat. NH4C1 solution and extracted with ethyl acetate (3 X 100 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified by combi flash columnchromatography to afford compound 15 (2.4 g, 60.6%) as an off white solid. TLC: 50% EtOAc/ hexane (Rf: 0.6); ‘H NMR (400 MHz, DMSO-d6): ö 10.42 (s, 1H), 7.40 (d, J= 7.6 Hz, 1H), 7.11 (d, J= 7.6 Hz, 1H), 6.98 (s, 1H), 1.85 - 1.82 (m, 2H), 1.65 - 1.63 (m, 5H), 1.53 - 1.48 (m, 3H), LCMS Observed (m/z): 279.95 (M+1).
References:
ASSEMBLY BIOSCIENCES, INC.;TURNER, William;ARNOLD, Lee, Daniel;LI, Leping;BURES, Mark;HAYDAR, Simon;MAAG, Hans;BANNEN, Lynne WO2018/53157, 2018, A1 Location in patent:Page/Page column 155; 156
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