Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:22])[CH:9]=[C:10]([C:11]3[CH:21]=[CH:20][C:14]4[O:15][CH2:16][CH2:17][N:18]([CH3:19])[C:13]=4[CH:12]=3)[C:3]=12.[CH3:23][N:24]1[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[N:25]1.CN(C)C1C=CC=CC=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:23][N:24]1[CH:28]=[CH:27][C:26]([S:29]([NH:32][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[N:8]([CH3:22])[CH:9]=[C:10]([C:11]4[CH:21]=[CH:20][C:14]5[O:15][CH2:16][CH2:17][N:18]([CH3:19])[C:13]=5[CH:12]=4)[C:3]=23)(=[O:31])=[O:30])=[N:25]1Alternatively, a mixture of 6-(4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine (130 mg, 0.363 mmol), 1-methyl-1H-pyrazole-3-sulfonamide (D94) (88 mg, 0.544 mmol), 2-(dimethylamino)-2′-(dicyclohexylphosphino)biphenyl (21.42 mg, 0.054 mmol), Pd2(dba)3 (24.92 mg, 0.027 mmol), cesium carbonate (355 mg, 1.089 mmol) in 1,4-dioxane (2.7 mL) was heated at 120° C. for 55 mins using a microwave reactor. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was separated, washed with brine, dried and concentrated. The residue was then purified on silica eluting with a gradient of 0-100% ethyl acetate in cyclohexane to afford a material which was further purified by MDAP (acidic condition) to afford the title compound (35 mg). LCMS (A): m/z (M+H)+ 439, C21H22N6O3S requires 438 (acidic).
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