Benzylamine → Benzyl-(3-bromo-6-methoxy-[1,5]naphthyridin-4-yl)-amine

HRID 2273211Notes

Reaction equation

[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[C:19](Br)=[C:18]2[C:13]([CH:14]=[CH:15][C:16]([O:21][CH3:22])=[N:17]2)=[N:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([NH:8][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[N:17]=2)[N:12]=[CH:11][C:10]=1[Br:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Benzylamine (67 mg, 0.63 mmol, 2.0 eq) is added at room temperature to a stirred solution of 7,8-dibromo-2-methoxy-[1,5]naphthyridine (100 mg, 0.31 mmol, 1.0 eq) in N,N-dimethylformamide (10 mL), followed by potassium carbonate (87 mg, 0.63 mmol, 2.0 eq). After 2 hours stirring at 120° C., solvent is removed and the residue is extracted with ethyl acetate (3×10 mL) and water (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give the crude product that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 5:1, v/v) to afford benzyl-(3-bromo-6-methoxy-[1,5]naphthyridin-4-yl)-amine as a light yellow solid (50 mg, 46% yield).

Workup

customsolvent is removed
extractionthe residue is extracted with ethyl acetate (3×10 mL) and water (10 mL)
dry with materialThe combined organic layers are dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto give the crude product that
customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record: ord-043e61bca5b24321b1f249a14a9d82fb
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120822B2

Reaction notes

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