(S)-4-((4-Chloro-3-methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl ester → (S)-4-((3-Methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl ester

HRID 449839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449839
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][N:9]2[C:17]3[CH:16]=[CH:15][C:14]([C:18]#[N:19])=[CH:13][C:12]=3[C:11]3[CH2:20][C@H:21]([NH:23][C:24](=[O:29])[O:25][CH:26]([CH3:28])[CH3:27])[CH2:22][C:10]2=3)[C:3]=1[O:30][CH3:31]>[Pd].CO.O>[CH:26]([O:25][C:24](=[O:29])[NH:23][C@@H:21]1[CH2:22][C:10]2[N:9]([CH2:8][C:4]3[C:3]([O:30][CH3:31])=[CH:2][CH:7]=[CH:6][N:5]=3)[C:17]3[CH:16]=[CH:15][C:14]([C:18]#[N:19])=[CH:13][C:12]=3[C:11]=2[CH2:20]1)([CH3:28])[CH3:27]

Komponenten

5

Edukt 1

HCID 66933264(S)-4-((4-Chloro-3-methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl ester

Produkt 1

HCID 66933193(S)-4-((3-Methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl esterAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysator2×HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of (S)-isopropyl 4-((4-chloro-3-methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamate (12.53 g, 28.55 mmol) and 10% palladium on carbon (1.00 g) in methanol (150 mL) is hydrogenated at 50 psi at room temperature overnight. A fresh batch of 10% palladium on carbon (1.2 g) is slurried in water (˜2 mL) and added to the reaction mixture, which is hydrogenated (50 psi) at room temperature overnight. The catalyst is filtered off and the solution is concentrated under reduced pressure to obtain a pale yellow solid. The solid is triturated with ether twice and dried under high vacuum to afford a yellow solid (10.80 g, 94%). LC-ES/MS m/z 405.2 [M+H]+

Aufarbeitung

  1. additionadded to the reaction mixture, which
  2. customat room temperature
  3. customovernight
  4. filtrationThe catalyst is filtered off
  5. concentrationthe solution is concentrated under reduced pressure
  6. customto obtain a pale yellow solid
  7. customThe solid is triturated with ether twice
  8. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6b96c004a33e4400bf50a82ed9b59c14
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486943B2

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