[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=O)[CH:10]=1)[N:7]([CH3:14])[CH:6]=[C:5]2[CH:15]([CH3:17])[CH3:16].[NH2:18][CH2:19][C:20]1[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=1[CH3:26].C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH:18][CH2:19][C:20]3[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=3[CH3:26])=[O:13])[CH:10]=1)[N:7]([CH3:14])[CH:6]=[C:5]2[CH:15]([CH3:17])[CH3:16]To a stirred suspension of 5-bromo-1-methyl-3-(1-methylethyl)-1H-indole-7-carboxylic acid (300 mg, 1.013 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (280 mg, 1.484 mmol) and HOAt (200 mg, 1.469 mmol) in DMF (15 mL) was added N-methylmorpholine (170 μL, 1.546 mmol) and EDC free base (310 mg, 1.997 mmol). The reaction was stirred for 18 h at RT. LCMS showed that the reaction was complete. The reaction was evaporated to near dryness under vacuum. Water (˜15 mL) was added and the solids which precipitated out were triturated, filtered and dried under vacuum. LCMS indicated that the solids were only 87% pure. The solid was partially dissolved in CH2Cl2. Noticed that the product began to crystallize out. Slowly added an equal volume of hexanes, triturated, filtered and dried under vacuum to give the product 5-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-methyl-3-(1-methylethyl)-1H-indole-7-carboxamide (188 mg, 0.437 mmol, 43.1% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=11.50 (br. s., 1H), 8.54 (t, J=4.8 Hz, 1H), 7.75 (d, J=1.8 Hz, 1H), 7.14 (s, 1H), 7.09 (d, J=2.0 Hz, 1H), 5.87 (s, 1H), 4.31 (d, J=5.1 Hz, 2H), 3.65 (s, 3H), 3.11 (dt, J=6.9, 13.5 Hz, 1H), 2.22 (s, 3H), 2.12 (s, 3H), 1.26 (d, J=6.8 Hz, 6H). MS (ES)+ m/e 429.9 [M+H]+.
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