[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[Na+].[Na+].C(O)C.FC1C=C([C:29]2[C:34](=[O:35])[N:33]3[CH:36]=[CH:37][S:38][C:32]3=[N:31][C:30]=2[CH3:39])C=C(F)C=1>C1(C)C=CC=CC=1.O>[CH3:39][C:30]1[N:31]=[C:32]2[S:38][CH:37]=[CH:36][N:33]2[C:34](=[O:35])[C:29]=1[C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1
This compound was prepared from Step 2 intermediate (10 g, 34.234 mmol), 4-cyanophenylboronic acid (6.5 g, 44.235 mmol), Pd[(C6H5)3P]4 (1.62 g, 1.401 mmol) and Na2CO3 (21.7 g, 2.051 mmol) in a mixture of toluene (250 ml), ethanol (150 ml) and water (100 ml) according to the procedure described in Intermediate 3, Step 3 to afford a crude product which was purified by silica gel column chromatography using 10% ethyl acetate in chloroform to give 5 g of the product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 2.19 (s, 3H), 7.53 (d, J=7.8 Hz, 3H), 7.88 (d, J=7.8 Hz, 2H) 8.02 (d, J=4.8 Hz, 1H); ESI-MS (m/z) 265.31 (M−H)−.
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