[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:21]1[N:22]=[C:23]([C:30]([C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[N:38]([CH3:42])[C:37](=[O:43])[N:36]([CH2:44][C:45]2[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=2)[C:35]3=[O:52])=[O:31])[N:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=12>O.CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:51][C:48]1[CH:49]=[CH:50][C:45]([CH2:44][N:36]2[C:35](=[O:52])[C:34]3[C:39](=[CH:40][CH:41]=[C:32]([C:30]([C:23]4[N:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]5=[C:21]([C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)[N:22]=4)=[O:31])[CH:33]=3)[N:38]([CH3:42])[C:37]2=[O:43])=[CH:46][CH:47]=10.04 g (0.32 mmol) of 3-pyridylboronic acid, 0.2 g (0.81 mmol) of potassium phosphate dihydrate dissolved in 0.29 ml of water, and 6.2 mg (0.01 mmol) of tetrakis(triphenylphosphine)palladium are added to 0.15 g (0.27 mmol) of 6-[(1-bromoimidazo[1,5-a]pyridin-3-yl)carbonyl]-3-(4-fluorobenzyl)-1-methylquinazoline-2,4(1H,3H)-dione in 3 ml of DMF under an inert argon atmosphere. The reaction medium is microwave-heated at 150° C. for 20 minutes. After filtration over talc, the reaction medium is concentrated under reduced pressure. The residue obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (95/5) mixture. 0.12 g of a yellow solid is obtained.
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