L-Alaninol → HCID 68294972, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with tert-butyl 7-chloro-3,4-dihydro-2,6-naphthyridine-2(1H)-carboxylate (175 mg, 0.651 mmol, CASRN 1060816-50-3), Pd2(dba)3 (29.8 mg, 0.0326 mmol), Binap-rac (40.5 mg, 0.0651 mmol), (S)-2-aminopropan-1-ol (97.8 mg, 1.30 mmol), and NaO-tert-Bu (125 mg, 1.30 mmol) and toluene (3 mL), sealed, degassed with nitrogen for 5 min then heated to 90° C. for 4 h. The reaction was cooled and filtered through a plug of CELITE. The filtrate was concentrated and the resulting residue was purified by reverse phase chromatography (SP4) eluting with a MeCN/H2O gradient (5-95% ACN) to afford 56 mg (28%) of (S)-tert-butyl 7-(1-hydroxypropan-2-ylamino)-3,4-dihydro-2,6-naphthyridine-2(1H)-carboxylate (326).

Provenance & Evidence