6-Benzyloxy-5-fluoro-1H-indole-2-carboxylic acid → 6-Benzyloxy-5-fluoro-1H-indole

HRID 1404080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1404080
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14](C(O)=O)[NH:15]2)=[CH:11][C:10]=1[F:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CN1CCCC1=O.[Cu]>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][C:10]=1[F:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 583038746-Benzyloxy-5-fluoro-1H-indole-2-carboxylic acid

Produkt 1

HCID 583039226-Benzyloxy-5-fluoro-1H-indoleAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A mixture of compound 4-2 (2.58 g, 9.07 mmol) and copper (2.97 g, 45.1 mmol) in 80 mL of 1-methylpyrrolidin-2-one was heated at reflux overnight under nitrogen. After cooling to room temperature, the mixture was filtered through Celite and washed with EtOAc. The filtrate was partitioned between water and EtOAc (2×150 mL). The combined organic phase was washed with water and brine, and then dried over anhydrous Na2SO4. The black residue was purified by column chromatography (hexanes/EtOAc 2% to 12%) to give compound 4-3 (1.31 g, 60%) as a white solid. 1H NMR (CDCl3, 300 MHz) □ 5.16 (s, 2H), 6.94-6.98 (m, 1H), 6.96 (d, 1H, J=7.1), 7.10-7.14 (m, 1H), 7.29-7.42 (m, 4H), 7.44-7.50 (m, 2H), 8.01 (bs, 1H). APCI [M−1]: 240.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight under nitrogen
  3. filtrationthe mixture was filtered through Celite
  4. washwashed with EtOAc
  5. customThe filtrate was partitioned between water and EtOAc (2×150 mL)
  6. washThe combined organic phase was washed with water and brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe black residue was purified by column chromatography (hexanes/EtOAc 2% to 12%)

Quellen und Nachweise

ORD-Eintrag
ord-b837f7bdda17476cb3f3a2991098f4c4
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912220B2

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