Hydrochloric Acid → 5-bromo-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide

HRID 661990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 661990
[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7](C(OCC)=O)[CH2:8][C:9]=1[NH:10]2.[CH3:23][Li].Cl.[CH2:26]1[CH2:30][O:29]CC1>>[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15]([NH2:16])=[O:17])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7]([C:30]([OH:29])([CH3:26])[CH3:23])[CH2:8][C:9]=1[NH:10]2

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 59375013ethyl 5-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate2×HCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 593750225-bromo-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamideAusbeute 89 %

Versuchsvorschrift

A solution of ethyl 5-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate (Intermediate 46-1, 2 g, 5.48 mmol) in THF (100 mL) cooled in an ice bath was treated with methyllithium (1.6 M in diethyl ether, 17.11 mL, 27.4 mmol). After 1 h, the mixture was treated slowly with a mixture of 1 M hydrochloric acid (20 mL) and ice (20 g). The organic layer was separated, and the aqueous layer was extracted twice with DCM. The combined organic phases were washed with water and brine, dried and concentrated. The residue was triturated with DCM to provide 5-bromo-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide as a light yellow solid (1.72 g, 89%). 1H NMR (400 MHz, methanol-d4) δ 7.38 (1H, d, J=8.14 Hz), 7.16 (1H, d, J=8.14 Hz), 3.37-3.45 (1H, m), 2.90-2.97 (1H, m), 2.79-2.89 (1H, m), 2.54-2.64 (1H, m), 2.20-2.28 (1H, m), 1.80-1.90 (1H, m, J=11.94, 11.94, 4.95, 2.20 Hz), 1.41-1.53 (1H, m, J=12.43, 12.43, 12.32, 5.28 Hz), 1.30 (6H, s). Mass spectrum m/z 351, 353 (M+H)+.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted twice with DCM
  3. washThe combined organic phases were washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was triturated with DCM

Quellen und Nachweise

ORD-Eintrag
ord-a6bdf52f440a4fedb1f85f666f126a68
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084620B2

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