2-Bromoethanol → 5-(6-(2-hydroxyethyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yloxy)-N-(3-(trifluoromethyl)phenyl)-1H-indole-1-carboxamide

Participants

Reaction Steps

5-(6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yloxy)-N-(3-(trifluoromethyl)phenyl)-1H-indole-1-carboxamide (125.9 mg, 0.287 mmol) is dissolved in DMF (5 mL) and TEA (80 μL, 0.577 mmol) is added followed by 2-bromoethanol (80 μL, 1.133 mmol). The solution is stirred at rt overnight. Then the reaction is concentrated and absorbed onto silica gel and separated via FCC (0-10%, 10% NH4 in MeOH:DCM) to obtain 5-(6-(2-hydroxyethyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yloxy)-N-(3-(trifluoromethyl)phenyl)-1H-indole-1-carboxamide. MS (ESI) m/z 484.0 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 10.38 (s, 1 H)8.56 (s, 1 H)8.27 (d, J=9.09 Hz, 1 H)8.09-8.14 (m, 2 H)7.97 (d, J=7.58 Hz, 1 H)7.65 (t, J=8.08 Hz, 1 H)7.48-7.52 (m, 2 H)7.15 (dd, J=8.84, 2.53 Hz, 1 H)6.80 (d, J=3.54 Hz, 1 H)4.57 (t, J=5.56 Hz, 1 H)3.98-4.03 (m, 4 H)3.58 (q, J=6.06 Hz, 2 H) 2.82 (t, J=6.06 Hz, 2 H).

Provenance & Evidence