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Pyridine → 3-Bromo-7-(ethylamino)-1-methyl-1,6-naphthyridin-2(1H)-one

HRID 710581
Notes
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Reaction equation

HRID 710581 reaction equation
[CH2:1]([NH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10](=[O:15])[N:11]2[CH3:14])=[CH:6][N:5]=1)[CH3:2].N1C=CC=CC=1.C1([Se][Br:29])C=CC=CC=1>C(Cl)Cl>[Br:29][C:9]1[C:10](=[O:15])[N:11]([CH3:14])[C:12]2[C:7]([CH:8]=1)=[CH:6][N:5]=[C:4]([NH:3][CH2:1][CH3:2])[CH:13]=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 123446BromoselenobenzeneHCID 673783687-(Ethylamino)-1-methyl-1,6-naphthyridin-2(1H)-one

Product 1

HCID 673783593-Bromo-7-(ethylamino)-1-methyl-1,6-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
39 °C

Procedure

To a solution of 7-(ethylamino)-1-methyl-1,6-naphthyridin-2(1H)-one (20 mg, 0.1 mmol) and pyridine (27 μL, 0.3 mmol) in DCM (2 mL) was added phenylselenium bromide (72 mg, 0.3 mmol). The mixture was heated at 39° C. for 6 h, and then the solvent was removed under vacuum. The residue was chromatographed on silica gel (30% ethyl acetate in hexanes eluant) to provide the title compound. MS (m/z) 282.0 (M+1).

Workup

  1. customthe solvent was removed under vacuum
  2. customThe residue was chromatographed on silica gel (30% ethyl acetate in hexanes eluant)

Sources & evidence

ORD record
ord-812fa3d5a0cb45b989bb734a57ddfeb3
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181238B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes