Sodium Carbonate → Methyl 3-cyclohexyl-2-phenyl-1H-indole-6-carboxylate

HRID 1713923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713923
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][CH3:20])=[O:18])[CH:5]=2.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>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][CH3:20])=[O:18])=[CH:7][CH:8]=3)[NH:3][C:2]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 11175076Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

Produkt 1

HCID 11416343Methyl 3-cyclohexyl-2-phenyl-1H-indole-6-carboxylateAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (from Step 3) 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 ultrasound for 30 min, then Pd(PPh3)4 (0.1 eq.) was added and mixture degassed with ultrasound for a further 30 min. The reaction was stirred under nitrogen at 90° C. for 6 h and then cooled to RT. Water was added and the solids filtered off. They were washed with Et2O to give the title compound (49%). The combined mother liquors together with the reaction solvents were washed with water (150 ml) and after phase-cut the organic phase was dried over Na2SO4 and evaporated to dryness. The residual solid was crystallized from boiling CHCl3 to give more title compound (38%, 87% total yield). 1H NMR (400 MHz, DMSO-d6, 300 K) δ 1.21-1.48 (m, 3H), 1.65-1.80 (m, 5H), 1.90-2.05 (m, 2H), 2.79-2.95 (m, 1H), 3.88 (s, 3H), 7.2-7.34 (m, 1H), 7.40-7.50 (m, 1H), 7.51-7.60 (m, 3H), 7.60 (d, J 7.6, 1H), 7.84 (d, J 7.6, 1H), 8.00 (s, 1H); MS (ES+) m/z 334 (M+H)+.

Aufarbeitung

  1. customThe mixture was degassed with ultrasound for 30 min
  2. custommixture degassed with ultrasound for a further 30 min
  3. temperaturecooled to RT
  4. additionWater was added
  5. filtrationthe solids filtered off
  6. washThey were washed with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-10098a1d69d247f08da3db77ebfbeabe
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795250B2

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