Sodium hydride → HCID 19601655, compound

Participants

Reaction Steps

To a solution of 1-(2-tributylstannylphenyl)-N-methyl-3-isoquinoline-carboxamide (105 mg, 0.19 mmol) in DMF (5 mL) was added 60% NaH (65 mg, 1.61 mmol) in one portion. The mixture was stirred under Ar at room temperature for 40 min. Then, 3-fluoropropyl bromide (124 μl, 1.67 mmol) was added. After stirring under Ar at room temperature for 24 h, the mixture was quenched by adding H2O (9 mL). The mixture was extracted with CH2Cl2 (3×15 mL). The combined organic layers were dried (MgSO4), filtered. The filtrate was concentrated in vacuo. The residue was chromatographed (SiO2, 5-10% ethyl acetate/hexane, 0.1% Et3N), thereby affording an oil (29.3 mg, 25%), and starting material (62.5 mg). 1H NMR (CDCl3) d 0.32-0.68 (m, 6 H, SnCH2), 0.70 (t, J=7.2 Hz, 9 H, CH3), 0.95-1.32 (m, 12 H, CH2CH2), 2.15-2.28 (m, 2 H, CH2), 3.13 (d, J=11.1 Hz, 3 H, N-methyl), 3.58-3.85 (m, 2 H, N--CH2), 4.48 (qt, J=123.9, 47.4, 5.7 Hz, 2 H, CH2F), 7.42-7.62 (m, 4 H, aromatic), 7.65-7.80 (m, 2 H, aromatic), 7.91-8.15 (m, 3 H, aromatic). HRFABMS Calcd. for C32H46FN2O12OSn: 613.2599. Found: 613.2619.

Provenance & Evidence