Sodium Hydroxide → 6-(6,7-Dimethoxy-quinolin-4-ylmethyl)-naphthalen-2-ylamine

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Reaction Steps

To a sealed tube, 4-(6-bromo-naphthalen-2-ylmethyl)-6,7-dimethoxy-quinoline (Step f, 100 mg, 0.11 mmol), Pd2(dba)3 (5 mg, 0.0055 mmol), P(t-Bu)3 (1.1 mg, 0.0055 mmol), toluene (1 mL) was combined under nitrogen, followed by addition of LiHMDS (1M in THF, 0.137 mL, 0.137 mmol). The reaction was stirred at RT overnight. The suspension was diluted with Et2O and HCl (1M, 1 mL) was added. The crude material was poured into 1N NaOH and extracted with Et2O 3×. The combined organic layer was washed with water and brine, dried on Na2SO4, filtered, concentrated and purified by prep-TLC with 100% EtOAc to give the desired compound. MS (ESI, pos. ion) m/z: 345.1 (M+1).

Provenance & Evidence