Water → HCID 89473219, compound

Participants

Reaction Steps

(S)-7-azido-3-bromo-5′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,4′-[1,3]oxazin]-2′-amine (200 mg, 0.517 mmol) was dissolved in MeOH (2 mL) and sodium borohydrate (195 mg, 5.17 mmol) was added at rt. After 1 h, additional MeOH (2 mL) and 10 equiv of NaBH4 were added at rt. The reaction mixture was allowed to stir overnight. Additional MeOH (2 mL) and 10 equiv of NaBH4 were added and the reaction was allowed to stir for 1 h. Water was added, followed by EtOAc. The organic phase was separated, dried over MgSO4. The solvent was removed under reduced pressure to give (S)-3-bromo-5′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,4′-[1,3]oxazine]-2′,7-diamine as a light-yellow solid. The compound was used in the next step without further purification. MS m/z=362.8 [M+H]+. Calculated for C15H13BrN4O2: 361.19.

Provenance & Evidence