Potassium Phosphate, Tribasic → 1-tert-Butyl 6-methyl 3-phenyl-1H-indole-1,6-dicarboxylate

HRID 409907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 409907
I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:22]1([C:2]2[C:10]3[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=3)[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 71278271-tert-butyl 6-methyl 3-iodo-1H-indole-1,6-dicarboxylateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Produkt 1

HCID 596260441-tert-Butyl 6-methyl 3-phenyl-1H-indole-1,6-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 1-tert-butyl 6-methyl 3-iodo-1H-indole-1,6-dicarboxylate 11a (5.02 mmol, 2.016 g), phenylboronic acid 10b (7.53 mmol, 0.92 g), Pd(OAc)2 (0.402 mmol, 90 mg), Sphos 0.904 mmol, (0.37 g), and K3PO4 (10.1 mmol, 2.13 g) in toluene (10 mL) in sealed reaction vial was stirred at room temperature for 2 min and then heated at 90° C. under N2 for 4 h. The reaction mixture was quenched with EtOAc and water. The organic layer was concentrated and purified by flash column chromatography (silica gel, 8% EtOAc/hexanes). The desired product was collected as a light yellow solid that was washed with small amount of hexanes to obtain 16a as a white solid.

Aufarbeitung

  1. customin sealed reaction vial
  2. temperatureheated at 90° C. under N2 for 4 h
  3. customThe reaction mixture was quenched with EtOAc and water
  4. concentrationThe organic layer was concentrated
  5. custompurified by flash column chromatography (silica gel, 8% EtOAc/hexanes)
  6. customThe desired product was collected as a light yellow solid
  7. washthat was washed with small amount of hexanes

Quellen und Nachweise

ORD-Eintrag
ord-13c863bdf2e14095b340d4c2a90cdb0e
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759533B2

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