Ethyl Acetate → tert-butyl 3-cyclohexyl-2-phenyl-1H-indole-6-carboxylate

HRID 1713950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713950
Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:5]=2.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>COCCOC.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:11]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:7][CH:8]=3)[NH:3][C:2]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 59750072tert-Butyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

Produkt 1

HCID 68436344tert-butyl 3-cyclohexyl-2-phenyl-1H-indole-6-carboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of tert-butyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (from Step 2) in DME and EtOH (0.2 M, 3:1, v/v) was added phenyl-boronic acid (1.2 eq.) followed by 2 M aqueous Na2CO3 (8.5 eq.). The mixture was degassed with argon, then Pd(PPh3)4 (0.1 eq.) was added and the mixture stirred under argon at 80° C. for 1 h. After cooling to RT, EtOAc was added and the organic layer washed with HCl solution (1N, ×2) and brine. The organic layer was dried over Na2SO4 and evaporated and the residue purified by silica gel chromatography (Flashmaster Personal, PE:EtOAc, 20:1) to give the title compound (90%). 1H NMR (400 MHz, DMSO-d6, 300 K) δ 1.21-1.48 (m, 3H), 1.56 (s, 9H), 1.65-1.80 (m, 5H), 1.90-2.05 (m, 2H), 2.79-2.95 (m, 1H), 7.50-7.57 (m, 6H), 7.40-7.50 (m, 1H), 7.79 (d, J 7.6, 1H), 7.94 (s, 1H); MS (ES+) m/z 376 (M+H)+.

Aufarbeitung

  1. customThe mixture was degassed with argon
  2. temperatureAfter cooling to RT
  3. washthe organic layer washed with HCl solution (1N, ×2) and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated
  6. customthe residue purified by silica gel chromatography (Flashmaster Personal, PE:EtOAc, 20:1)

Quellen und Nachweise

ORD-Eintrag
ord-bbbf495304864bc18a15f70b28836100
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795250B2

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