[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[C:14](I)=[CH:15][N:16]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]2=[CH:10][CH:9]=1.[CH3:28][S:29]([C:32]1[N:37]=[C:36]([N:38]2[CH2:43][CH2:42][CH:41]([NH:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[CH2:40][CH2:39]2)[CH:35]=[C:34]([Sn](C)(C)C)[N:33]=1)(=[O:31])=[O:30]>CN(C=O)C.C(Cl)Cl.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.[Cu]I>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[C:14]([C:34]3[N:33]=[C:32]([S:29]([CH3:28])(=[O:30])=[O:31])[N:37]=[C:36]([N:38]4[CH2:43][CH2:42][CH:41]([NH:44][C:45](=[O:51])[O:46][C:47]([CH3:49])([CH3:48])[CH3:50])[CH2:40][CH2:39]4)[CH:35]=3)=[CH:15][N:16]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]2=[CH:10][CH:9]=1A glass microwave reaction vessel was charged with 5-(2-fluorophenyl)-3-iodo-1-tosyl-1H-pyrrolo[3,2-b]pyridine (100 mg, 0.203 mmol) and tert-butyl 1-(2-(methylsulfonyl)-6-(trimethylstannyl)pyrimidin-4-yl)piperidin-4-ylcarbamate (105 mg, 0.203 mmol) in DMF (1.5 mL) followed by Pd(PPh3)4 (11.74 mg, 10.16 μmol) and CuI (7.8 mg, 0.041 mmol). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 100° C. for 1 h. The mixture was diluted with DCM and washed with water, and brine. The organic layer was dried with MgSO4, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 20-80% EtOAc in hexanes) to give tert-butyl 1-(6-(5-(2-fluorophenyl)-1-tosyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-2-(methylsulfonyl)pyrimidin-4-yl)piperidin-4-ylcarbamate (86 mg, 0.119 mmol, 58.7% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 721.0 (M+1).
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