Acetic Acid → tert-Butyl 6-bromo-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate

HRID 225847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 225847
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(O)=O.C1C(=O)N([Br:29])C(=O)C1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([Br:29])=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 11831362tert-Butyl 3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate

Produkt 1

HCID 11833959tert-Butyl 6-bromo-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(tert-butoxycarbonyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (1.37 g, 5.85 mmole) in CH2Cl2 (30 mL) was added glacial HOAc (3.4 mL, 58.5 mmole) and NBS (1.09 g, 6.14 mmole). After 72 hr the mixture was washed with 2.0 M NaOF, H2O, and brine. The mixture was dried (MgSO4), filtered, and concentrated under reduced pressure to give the title compound (1.79 g, 98%) which was sufficiently pure for use in the next step: 1H NMR (400 MHz, CDCl3) δ 8.35 (s, 1 H), 7.51 (s, 1 H), 3.77 (m, 2 H), 2.75 (t, J=6.5 Hz, 2 H), 1.93 (m, 2 H), 1.54 (s, 9 H).

Aufarbeitung

  1. washAfter 72 hr the mixture was washed with 2.0 M NaOF, H2O, and brine
  2. dry with materialThe mixture was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-58fa3a77db1f45cb863eed42ab085058
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557125B2

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