[NH2:1][C:2]1[C:3]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([F:23])[CH:14]=2)=[N:4][C:5]([C:8]2[CH:9]=[N:10][NH:11][CH:12]=2)=[CH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH3:32]>CN(C=O)C>[NH2:1][C:2]1[C:3]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([F:23])[CH:14]=2)=[N:4][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:31][CH3:32])[CH:12]=2)=[CH:6][N:7]=1To methyl 4-(3-amino-6-(1H-pyrazol-4-yl) pyrazin-2-yl)-2-fluorobenzoate (45 mg, 0.115 mmol) in DMF (2 mL) was added potassium carbonate (47.6 mg, 0.345 mmol), followed by bromoethane (0.017 mL, 0.230 mmol). The reaction mixture was stirred at room temperature for 48 h. The reaction mixtures was partitioned between ethylacetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered, evaporated and purified by flash chromatography eluting with 0-60% of EtOAc (contains 10% of MeOH)/heptane to yield the desired product (25 mg, 64%, 80% purity). LCMS (m/z): 342.0 (MH+), 0.73 min.
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