Sodium borohydride → (5-Aminobenzo[f][1,7]naphthyridin-8-yl)methanol

HRID 340299Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH:12]=[CH:13][C:14]([C:16](OC)=[O:17])=[CH:15][C:4]=2[N:3]=1.[BH4-].[Na+]>CCO>[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH:12]=[CH:13][C:14]([CH2:16][OH:17])=[CH:15][C:4]=2[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 5-aminobenzo[f][1,7]naphthyridine-8-carboxylate (from the previous step) (1.0 eq.) in EtOH (0.03M) was added NaBH4 (10 eq.) at 25° C. The solution was heated to 80° C. for 5 hours. After cooling to ambient temperature, the reaction mixture was concentrated en vacuo. The residue was portionized between saturated NaHCO3 and EtOAc. The layers were separated and aqueous layer was extracted with EtOAc twice. The combined organic layer was washed with brine, dried over MgSO4 and concentrated en vacuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-10% MeOH/DCM to give (5-aminobenzo[f][1,7]naphthyridin-8-yl)methanol as an off white solid: 1H NMR (methanol-d4): δ 8.82 (dd, 1H), 8.77 (dd, 1H), 7.26 (d, 1H), 7.70 (dd, 1H), 7.50 (d, 1H), 7.27 (dd, 1H), 4.66 (s, 2H). LRMS [M+H]=226.1.

Workup

temperatureAfter cooling to ambient temperature
concentrationthe reaction mixture was concentrated en vacuo
customThe layers were separated
extractionaqueous layer was extracted with EtOAc twice
washThe combined organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated en vacuo
customto obtain a crude residue
customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record: ord-eba1736d3b434dbdbf712343a96bcc38
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895577B2

Reaction notes

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