o-Chlorophenylacetic acid → 3-{1-[(2-chlorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}thieno[3,2-c]pyridin-4-amine

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Reaction Steps

To a 4 mL screw cap vial was added 3-(2,3-dihydro-1H-indol-5-yl)thieno[3,2-c]pyridin-4-amine (100 mg, 0.374 mmol) followed by HATU (142 mg, 0.374 mmol), 2-chlorophenylacetic acid (63.8 mg, 0.374 mmol) and DIEA (0.261 mL, 1.496 mmol). N,N-Dimethylformamide (DMF) (2 mL) was added and the reaction was sealed and left to stir at room temperature overnight. The reaction mixture was poured into water (4 mL) and extracted with EtOAc (5 mL). The organics were dried over Na2SO4 and concentrated. The residue was taken up in DCM and purified via normal phase chromatography (0-10% MeOH/DCM). Fractions were collected and concentrated to afford 3-{1-[(2-chlorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}thieno[3,2-c]pyridin-4-amine (85.3 mg) as a pink solid. LC/MS (ES) m/z=420.2 [M+H]+ 1H NMR (400 MHz, DMSO-d6) δ ppm 3.28 (t, J=8.34 Hz, 2H) 4.02 (s, 2H) 4.32 (t, J=8.46 Hz, 2H) 5.43 (br. s., 2H) 7.23 (d, J=8.08 Hz, 1H) 7.26 (d, J=5.56 Hz, 1H) 7.31-7.37 (m, 3H) 7.39-7.44 (m, 2H) 7.45-7.51 (m, 1H) 7.83 (d, J=5.56 Hz, 1H) 8.11 (d, J=8.08 Hz, 1H).

Provenance & Evidence