o-Bis(bromomethyl)benzene → (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-(isoindolin-2-yl)pyrrolidine-2-carboxamide

Participants

Reaction Steps

Proceeding as in Example 7, but substituting 1,2-bis(bromomethyl)benzene and (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-amino-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide gave Compound 260, (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-(isoindolin-2-yl)pyrrolidine-2-carboxamide (47 mg, 0.088 mmol, 11%). 1H-NMR (400 MHz, DMSO-d6): 10.10 (s, 1H), 8.45 (s, 1H), 7.96 (s, 1H), 7.60 (d, J=10.0 Hz, 2H), 7.29-7.17 (m, 6H), 7.03-6.95 (m, 4H), 5.34-5.30 (m, 2H), 4.56-4.52 (m, 1H), 3.95 (s, 4H), 3.71-3.60 (m, 1H), 3.52-3.46 (m, 2H), 2.31-2.24 (m, 1H), 2.17-2.09 (m, 1H). MS (EI) for C29H27FN6O3. found 527.2 (MH+).

Provenance & Evidence