[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[C:12](/[CH:14]=[C:15](\[O-:17])/[CH3:16])#[N:13].[Na+].C(O)(=O)C.O>ClCCl.N1CCCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6](/[CH:10]=[C:14](/[C:15](=[O:17])[CH3:16])\[C:12]#[N:13])=[CH:7][CH:8]=2)[CH:3]=[N:2]1
10 g (68.4 mmol) 1H-indazole-5-carbaldehyde [preparation described in US 2005/0227968-A1 (Intermediate 1)], 7.91 g (75.2 mmol) sodium (1Z)-1-cyanoprop-1-en-2-olate, 4.89 ml (85.5 mmol) acetic acid and 0.68 ml (6.84 mmol) piperidine in dry dichloromethane (500 ml) were stirred at reflux temperature for 7 h using an inverse water separator. Upon cooling, a precipitate was formed which was collected by filtration and washed with dichloromethane. The solid was dried in vacuo to afford the crude title compound (19 g, 75% purity by LC-MS, 96% of th.) which was used in subsequent steps without further purification.
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