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

HRID 2273211
Notes
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Reaction equation

HRID 2273211 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 672578837,8-Dibromo-2-methoxy-[1,5]naphthyridine

Product 1

HCID 67255893Benzyl-(3-bromo-6-methoxy-[1,5]naphthyridin-4-yl)-amineYield 46.9%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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

  1. customsolvent is removed
  2. extractionthe residue is extracted with ethyl acetate (3×10 mL) and water (10 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product that
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes