2-Bromopyridine 1-oxide → 2-(7-(4-(tert-Butoxycarbonylamino)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridine 1-oxide

HRID 1711109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711109
[F:1][C:2]1[CH:3]=[C:4]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16](I)[S:17][C:10]=12.Br[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N+:29]=1[O-:34]>O1CCOCC1.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>[C:22]([O:21][C:20]([NH:19][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[CH:15]=[C:16]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N+:29]=4[O-:34])[S:17][C:10]=23)=[C:2]([F:1])[CH:3]=1)=[O:26])([CH3:25])([CH3:24])[CH3:23]

Komponenten

5

Edukt 2

HCID 3000572-Bromopyridine 1-oxideHCID 59457739HCID 59457739, Verbindung

Produkt 1

HCID 687168072-(7-(4-(tert-Butoxycarbonylamino)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridine 1-oxideAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 431 (460 mg, 0.94 mmol), 2-bromopyridine N-oxide (420 mg, 2.41 mmol), bistrimethyltin (294 μL, 465 mg, 1.42 mmol) and Pd(PPh3)4 (109 mg, 0.09 mmol) in dioxane (10 mL) was heated to reflux for 8 hrs under nitrogen. The reaction mixture was concentrated and purified by flash chromatography using the gradient 5-20% MeOH in EtOAc as an eluent yielding 432 (243 mg, 57% yield). LCMS: (M+H) 454.1.

Aufarbeitung

  1. temperatureto reflux for 8 hrs under nitrogen
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c4117b8a060b412f8c8c678f2c3361ee
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790729B2

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