Tetramethyltin → 3-Isoquinolinecarboxylic acid, 4-hydroxy-1-methyl-7-phenoxy-, methyl ester

HRID 1481116

Reaktionsgleichung

Reaktionsgleichung von HRID 1481116
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](Br)[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[Sn](C)(C)(C)[CH3:25]>CN1CCCC1=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH3:25])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4]

Komponenten

4

Edukt 2

HCID 11661TetramethyltinHCID 89813003Methyl 1-bromo-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Produkt 1

HCID 712448953-Isoquinolinecarboxylic acid, 4-hydroxy-1-methyl-7-phenoxy-, methyl esterAusbeute 58,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To a mixture of 1-bromo-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (500 mg, 1.34 mmol) in N-methylpyrrolidone (NMP) (7 mL) was added SnMe4 (358 mg, 2.0 mmol) and resin-bound-Pd(PPh3)2Cl2 (Sigma-Aldrich) (1-2 mmol/g) (40 mg, ca. 0.03 mmol). The resultant mixture was stirred in a 130° C. oil bath for 3 h. Reaction mixture was filtered and rinsed with NMP (1 mL). Filtrate was poured into water (120 mL) and stirred at room temperature until good precipitate formed. Solid was collected and rinsed with water (100 mL) and then hexanes (50 mL). Solid was dried and purified by silica gel chromatography, eluting with 2-50% EtOAc/hexanes, to provide the title compound 240 mg (0.78 mmol) in 58% yield. 1H NMR (200 MHz) CDCl3, δ in ppm: 11.68 (s, 1H), 8.37 (d, J=9.3 Hz, 1H), 7.48-7.08 (m, 7H), 4.07 (s, 3H), 2.75 (s, 3H).

Aufarbeitung

  1. customReaction mixture
  2. filtrationwas filtered
  3. washrinsed with NMP (1 mL)
  4. additionFiltrate was poured into water (120 mL)
  5. customformed
  6. customSolid was collected
  7. washrinsed with water (100 mL)
  8. customSolid was dried
  9. custompurified by silica gel chromatography
  10. washeluting with 2-50% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-962b33ddd8fe4c9894890c285bb31bdf
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409892B2

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