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Ethyl 5-bromopyridine-3-carboxylate → 5-[3-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]nicotinic acid ethyl ester

HRID 603019
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 603019
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15](B3OC(C)(C)C(C)(C)O3)[CH:16]=2)[N:11]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[CH:10]=1.[CH2:37]([O:39][C:40](=[O:48])[C:41]1[CH:46]=[C:45](Br)[CH:44]=[N:43][CH:42]=1)[CH3:38].C([O-])(O)=O.[Na+]>C(#N)C>[CH2:37]([O:39][C:40](=[O:48])[C:41]1[CH:46]=[C:45]([C:15]2[CH:16]=[C:17]3[C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])=[CH:10][N:11]([S:27]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)(=[O:28])=[O:29])[C:12]3=[N:13][CH:14]=2)[CH:44]=[N:43][CH:42]=1)[CH3:38]
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Komponenten

5

Edukt 3

HCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 516892Sodium BicarbonateHCID 160390673-(2-Methoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 596999005-[3-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]nicotinic acid ethyl esterAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Into a 20 mL Personal Chemistry microwave reaction vial were added 3-(2-Methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.995 g, 2.18 mmol), 5-Bromo-nicotinic acid ethyl ester (0.645 g, 2.33 mmol), 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichloromethane adduct (95.5 mg, 0.117 mmol), acetonitrile (10 ml) and saturated aqueous NaHCO3 (10 mL). The vial was sealed, purged, with N2, and irradiated in a Personal Chemistry Optimizer at 90° C. for 15 min. The layers were separated, and the aqueous phase was extracted 3× with EtOAc. The combined organic phase was treated with brine, dried (Na2SO4), filtered and concentrated. Purification by flash silica gel chromatography using a gradient of ethyl acetate and hexanes afforded 5-[3-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]nicotinic acid ethyl ester as a white powder (0.794 g, 69%). MS: m/z 528.1 [MH+].

Aufarbeitung

  1. customInto a 20 mL Personal Chemistry microwave reaction
  2. customThe vial was sealed
  3. custompurged, with N2
  4. customirradiated in a Personal Chemistry Optimizer at 90° C. for 15 min
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted 3× with EtOAc
  7. additionThe combined organic phase was treated with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by flash silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-de99d077aa1744c283b436303b1854c9
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07906648B2

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