Sodium Sulfate → HCID 67464623, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(6-formylpyridin-3-yl)-1-isopropyl-3-methyl-1H-indole-4-carboxamide (100 mg, 0.219 mmol), in DCM (10 mL) and methanol (2 mL) was added pyrrolidine (0.035 mL, 0.438 mmol), followed by sodium sulfate (31.1 mg, 0.219 mmol). The reaction stirred at rt for 12 h, at which time sodium borohydride (16.57 mg, 0.438 mmol) was added and the reaction stirred rt for 2 h and 45° C. for 2 h. The reaction was quenched with water and extracted with EtOAc. The organic layer was evaporated. Purification by reverse phase Gilson HPLC (10-60% acetonitrile/water+0.1% TFA, YMC ODS-A C18 Column 75×30 mm ID S-5 um, 12 nM Column 7 minutes), followed by isolation and extraction with EtOAc/0.1 N NaOH provided N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-3-methyl-6-(6-(pyrrolidin-1-ylmethyl)pyridin-3-yl)-1H-indole-4-carboxamide, which was evaporated from the organic layer as a yellow foam solid (68 mg, 0.125 mmol, 57.0% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.48 (br. s., 1 H) 9.06 (d, J=2.02 Hz, 1 H) 8.30 (dd, J=8.08, 2.27 Hz, 1 H) 8.20 (t, J=5.18 Hz, 1 H) 7.94 (d, J=1.26 Hz, 1 H) 7.60 (d, J=8.08 Hz, 1 H) 7.40 (s, 1 H) 7.32 (s, 1 H) 5.88 (s, 1 H) 4.92-4.89 (m, 1 H) 4.59 (d, J=5.56 Hz, 2 H) 4.36 (d, J=5.05 Hz, 2 H) 3.34 (br. s., 4 H) 2.25 (s, 3 H) 2.17 (d, J=1.01 Hz, 3 H) 2.11 (s, 3 H) 1.99 (br.s., 4 H) 1.45 (d, J=6.57 Hz, 6 H). LCMS: [M+H]+=512.3.

Provenance & Evidence