Acetic Acid → 3-Bromo-7-(2-pyrrolidin-1-yl-ethyl)[1,5]naphthyridine

HRID 273243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 273243
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:12][CH:13]=O)[CH:8]=[N:9]2)=[N:4][CH:3]=1.C(O)(=O)C.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[C:7]([CH2:12][CH2:13][N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH:6]=2

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 21043926(7-Bromo-1,5-naphthyridin-3-yl)acetaldehyde

Produkt 1

HCID 104028693-Bromo-7-(2-pyrrolidin-1-yl-ethyl)[1,5]naphthyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of the product from Example 153D (0.1 g, 0.4 mmol), acetic acid (0.4 mmol, 0.025 g) and pyrrolidine (0.44 mmol, 0.031 g) in dry THF (5 ml) NaBH(OAc)3 was added (0.6 mmol, 0.127 g). After 12 hr at room temperature the mixture was diluted with 50 mL of CH2Cl2 and washed successively with a saturated solution of sodium bicarbonate, brine and water. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified over silica using 10% MeOH in CH2Cl2. The desired compound was obtained in 40%. 1H NMR (CDCl3, 300 MHz) δ 1.60 (m, 4H), 2.20 (m, 4H), 2.75 (m, 4H), 8.30 (m, 1H), 8.40 (m, 1H), 8.90 (m, 1H), 9.05 (m, 1H). MS (ESI) [M+H]+ at 307.

Aufarbeitung

  1. washwashed successively with a saturated solution of sodium bicarbonate, brine and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified over silica using 10% MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-c3faa1c2c0c543ebba0d3033dcf48bee
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456196B2

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