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Cesium fluoride → Methyl 2-chloro-4-methyl-6-(3-methyl-1-tosyl-1H-indol-4-yl)nicotinate

HRID 80819
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 80819
[Cl:1][C:2]1[N:11]=[C:10](Cl)[CH:9]=[C:8]([CH3:13])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2B2OC(C)(C)C(C)(C)O2)[N:17]([S:33]([C:36]2[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH:16]=1.[F-].[Cs+]>CN(C=O)C.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>[Cl:1][C:2]1[N:11]=[C:10]([C:22]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:23]=2[C:15]([CH3:14])=[CH:16][N:17]3[S:33]([C:36]2[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH:9]=[C:8]([CH3:13])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]
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Komponenten

6

Edukt 3

HCID 25953Cesium fluorideHCID 46911843Methyl 2,6-dichloro-4-methylnicotinateHCID 712404273-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indole

Produkt 1

HCID 86690266Methyl 2-chloro-4-methyl-6-(3-methyl-1-tosyl-1H-indol-4-yl)nicotinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of methyl 2,6-dichloro-4-methylnicotinate (0.250 g, 1.14 mmol), 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indole (Example 6) (0.514 g, 1.25 mmol), Pd(Ph3P)4 (0.131 g, 0.114 mmol), and CsF (0.345 g, 2.27 mmol), in DMF (5 mL) was heated at 110° C. for 6 h. At that time the vessel was removed from the oil bath and allowed to cool to rt. The mixture was diluted with brine (50 mL) and EtOAc (50 mL). The layers were mixed and then separated. The aqueous layer was further extracted with EtOAc (50 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was then purified via FCC (0-10% EtOAc/heptane) to give the title compound. MS ESI m/z 469.0 & 470.9 (M+H)+.

Aufarbeitung

  1. customAt that time the vessel was removed from the oil bath
  2. additionThe mixture was diluted with brine (50 mL) and EtOAc (50 mL)
  3. additionThe layers were mixed
  4. customseparated
  5. extractionThe aqueous layer was further extracted with EtOAc (50 mL)
  6. dry with materialthe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was then purified via FCC (0-10% EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-ebf578b16e9146c59bf97ba1928ff07a
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846656B2

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