CON(C)[C:4](=[O:19])[C:5]1[CH:10]=[C:9]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[N:7][CH:6]=1.[H-].C([Al+]CC(C)C)C(C)C.CO.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[C:13]1([C:12]#[C:11][C:9]2[CH:10]=[C:5]([CH:4]=[O:19])[CH:6]=[N:7][CH:8]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
Charge an oven dried round bottom flask under nitrogen with a solution of N-methoxy-N-methyl-5-phenylethynylnicotinamide (2.00 g, 7.51 mmol), (prepared essentially as described in PREPARATION 2), in anhydrous toluene (20 mL) and cool to −78° C. Add a 1 M solution of diisobutylaluminum hydride in toluene (18 mL, 18 mmol) dropwise over 30 min and stir for an additional 30 min. Rapidly add methanol (15 mL) and warm to room temperature. Pour the reaction mixture into 100 mL of a saturated aqueous solution of Rochelle salt (potassium sodium tartrate) and stir vigorously for about 30 min. Upon standing, separate the organic layer, dry (magnesium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with 50:50 hexanes:ethyl acetate, to obtain the title compound as a white solid (1.2 g, 77%).
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