Ethanol → methyl 6-chloro-5-(4-(2-hydroxypropan-2-yl)-3-methoxyphenyl)-1H-indole-3-carboxylate

HRID 338360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338360
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[C:4]([O:12][CH3:13])[CH:3]=1.[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][NH:21]2)=[CH:17][C:16]=1B1OCC(C)(C)CO1.C(O)C.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCCC1>[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][NH:21]2)=[CH:17][C:16]=1[C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[C:4]([O:12][CH3:13])[CH:3]=1

Komponenten

8

Edukt 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 86698665methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylateHCID 866987012-(4-Bromo-2-methoxyphenyl)propan-2-ol

Produkt 1

HCID 86698700methyl 6-chloro-5-(4-(2-hydroxypropan-2-yl)-3-methoxyphenyl)-1H-indole-3-carboxylateAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

To a solution of 2-(4-bromo-2-methoxyphenyl)propan-2-ol (50.0 mg, 0.20 mmol) in toluene (0.81 mL) was added methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (72 mg, 0.22 mmol), ethanol (0.43 mL), and tetrahydrofuran (0.43 mL). This was followed by the addition of 2M potassium carbonate aqueous (0.58 mL, 1.2 mmol). The reaction was evacuated and back filled with nitrogen (3×) then Pd(dppf)Cl2 (19.0 mg, 0.023 mmol) was added and the reaction heated to 115° C. for 3 hours. The reaction was then cooled to room temperature and filtered through a pad of celite washing with ethyl acetate. The filtrate was concentrated under reduced pressure and purified via column chromatography (0-40% ethyl acetate/heptanes) to provide the title compound (45 mg, 59% yield) as a solid.

Aufarbeitung

  1. customThe reaction was evacuated
  2. additionback filled with nitrogen (3×)
  3. temperatureThe reaction was then cooled to room temperature
  4. filtrationfiltered through a pad of celite
  5. washwashing with ethyl acetate
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified via column chromatography (0-40% ethyl acetate/heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-e75f4f08af3f447a8a6019a7c6aff184
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889730B2

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