Sodium Carbonate → methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(4-methoxyphenyl)-1H-indole-6-carboxylate

HRID 1713929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713929
Br[C:2]1[N:3]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[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][CH3:20])=[O:18])[CH:5]=2.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.CCOC(C)=O.[Cl-].[Na+].O.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>[C:25]([O:24][C:22](=[O:23])[CH2:21][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2)[C:10]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:2]1[C:34]1[CH:35]=[CH:36][C:31]([O:30][CH3:29])=[CH:32][CH:33]=1)([CH3:28])([CH3:27])[CH3:26]

Komponenten

9

Edukt 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 299433152-Bromo-1-tert-butoxycarbonylmethyl-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester

Produkt 1

HCID 11340537methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(4-methoxyphenyl)-1H-indole-6-carboxylateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution (0.1 M) of methyl 2-bromo-1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylate (from Step 1) in DME and EtOH (5:2) was treated with 4-methoxyphenylboronic acid (1.5 eq.). Aqueous Na2CO3 (2 N, 8.5 eq.) was added and the solution was degassed, and then heated with Pd(PPh3)4 (0.1 eq.). The mixture was heated at 80° C. for 2 h, then cooled and diluted with EtOAc and brine. The organic phase was separated, dried and concentrated under reduced pressure. The residue was purified by filtration through silica gel (5:95 EtOAc/PE) to give the title compound (81%) as a solid. 1H NMR (300 MHz, DMSO-d6, 300K) δ 1.13-1.38 (m, 3H), 1.33 (s, 9H), 1.61-1.96 (m, 7H), 2.55-2.67 (m, 1H), 3.86 (s, 3H), 3.88 (s, 3H), 4.73 (s, 2H), 7.11 (d, J 8.6, 2H), 7.27 (d, J 8.6, 2H), 7.69 (dd, J 8.4, 1.1, 1H), 7.86 (d, J 8.4, 1H), 8.06 (d, J 1.1, 1H).

Aufarbeitung

  1. customthe solution was degassed
  2. temperaturecooled
  3. customThe organic phase was separated
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe residue was purified by filtration through silica gel (5:95 EtOAc/PE)

Quellen und Nachweise

ORD-Eintrag
ord-4182c14e3dee4ccda58bf50118c58504
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795250B2

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