[ClH:1].ClC1NC=C([C@H:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][NH:9]2)C1.[C:17]([O-:20])([O-])=[O:18].[K+].[K+].BrCCC=C1C2[CH:34]=[CH:35][CH:36]=[N:37][C:32]=2COC2C=CC(C(O)(C)C)=CC1=2>C(#N)C.O>[C:11]([O:20][C:17]([N:37]1[CH2:36][CH2:35][C@@H:34]([N:9]2[CH2:8][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:1])[CH:15]=3)[CH2:10]2)[CH2:32]1)=[O:18])([CH3:16])([CH3:12])[CH3:10]To a solution of (R)-5-chloro-2-pyrrolin-3-yl-2,3-dihydro-1H-isoindole hydrochloride (0.052 g, 0.23 mmol) in acetonitrile/water (8:2) (2 mL) was added K2CO3 (0.215 g, 1.5 mmol) and 2-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (0.079 g, 0.21 mmol). The solution was allowed to stir at room temperature for 48 h. The reaction was concentrated down and partitioned between EtOAc/H2O, extracted with EtOAc (3×). The organics were collected together dried over Mg2SO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (5% methanol/95% methylene chloride to 10% methanol/90% methylene chloride to 15% methanol/85% methylene chloride) to yield the title compound (0.055 g, 55%). 1H-NMR (CDCl3): δ 1.55(s, 9H), 1.77 (m, 1H), 2.02 (m, 2H), 2.37(pentet, 3H), 2.42–2.64 (m, 4H), 2.81 (t, 1H), 3.17 (pentet, 1H), 3.43 (s, 3H), 3.84 (s, 4H), 5.26 (bs, 2H), 6.11 (t, 1H), 6.79 (d, 1H), 7.08–7.28 (m, 5H), 7.43 (s, 1H), 7.56 (d, 1H), 8.46 (d, 1H). ESI-MS m/z: 516.02 (M+1), retention time 1.26.
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