[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(C(C)C)CC)(C)C.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]2[CH2:21][NH:22][CH2:23][C:16]=12>C(Cl)Cl>[CH3:1][S:2]([N:22]1[CH2:21][C:17]2[C:16](=[N:15][CH:20]=[CH:19][CH:18]=2)[CH2:23]1)(=[O:4])=[O:3]Methanesulfonyl chloride (0.97 mL, 12.4 mmol) was added dropwise to a −10° C. solution of diisopropyl-ethylamine (5.16 mL, 31.1 mmol) and 6,7-dihydro-5H-pyrrolo[3,4-b]pyridine (2.0 g, 10.0 mmol) in CH2Cl2 (20 mL). The mixture was stirred overnight at rt diluted with CH2Cl2 (300 mL) and washed with saturated aqueous sodium bicarbonate. The organic phase was separated, dried (MgSO4) and filtered through a short silica gel pad with EtOAc rinse. The filtrate was concentrated to yield 2.15 g (quantitative) of Ex 10-Step 1 product as a solid which was used without further purification: LCMS m/z 199.2 (M+1); 1H NMR (400 MHz, CDCl3) δ 8.54 (d, J=4.9, 1H), 7.61 (d, J=7.8, 1H), 7.25 (dd, J=7.8, 5.1, 1H), 4.75 (AB quartet, JAB=2.1, ΔvAB=7.8, 4H), 2.94 (s, 3H).
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