Cl[C:2]1[N:3]=[C:4]([O:29][CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[C:5]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([C:17]([NH:19][CH3:20])=[O:18])=[N:15][CH:16]=3)=[CH:9][N:8](COCC[Si](C)(C)C)[C:6]=2[N:7]=1.[NH2:36][C:37]1[CH:47]=[CH:46][C:40]([C:41]([N:43]([CH3:45])[CH3:44])=[O:42])=[CH:39][C:38]=1[CH3:48].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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].O1CCOCC1>[CH3:44][N:43]([CH3:45])[C:41]([C:40]1[CH:46]=[CH:47][C:37]([NH:36][C:2]2[N:3]=[C:4]([O:29][CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:5]3[C:10]([C:11]4[CH:12]=[CH:13][C:14]([C:17]([NH:19][CH3:20])=[O:18])=[N:15][CH:16]=4)=[CH:9][NH:8][C:6]=3[N:7]=2)=[C:38]([CH3:48])[CH:39]=1)=[O:42]5-(2-Chloro-4-(tetrahydro-2H-pyran-4-yloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-N-methylpicolinamide (1 equiv), 4-amino-N,N,3-trimethylbenzamide (1 equiv), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.2 equiv), cesium carbonate (2 equiv), tris(dibenzylideneacetone)dipalladium(0) (0.1 equiv) and 1,4-dioxane (0.2 M) were combined in a microwave vial and irradiated heated at 150° C. for 30 min. The mixture was concentrated and purified by flash chromatography 0-55% (Hex:EtOAc-800 mL), followed by 5-15% B (DCM:MeOH-800 mL) in the same run. Fractions were combined, concentrated and the compound was deprotected according to General Procedure A. The reaction mixture was concentrated and purified to give the title compound (21% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.92 (d, J=1.95 Hz, 1 H), 8.20 (dd, J=7.81, 1.56 Hz, 1 H), 8.07 (dd, J=16.59, 8.39 Hz, 2 H), 7.22-7.31 (m, 3 H), 5.49 (s, 1 H), 3.78-3.88 (m, 2 H), 3.52-3.61 (m, 2 H), 3.07 (s, 6 H), 2.96 (s, 3 H), 2.35 (s, 3 H), 2.08 (d, J=13.28 Hz, 2 H), 1.73-1.84 (m, 2 H). MS (ESI) m/z 530.0 [M+1]+.
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