StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-(4-Bromo-2-fluoro-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester

HRID 1366773
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1366773
[CH2:1]([O:3][C:4]([C:6]1[S:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1OS(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)(=O)=O)=[O:5])[CH3:2].[Br:32][C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[C:35]([F:40])[CH:34]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[S:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:37][C:36]1[CH:38]=[CH:39][C:33]([Br:32])=[CH:34][C:35]=1[F:40])=[O:5])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1230504-Bromo-2-fluoroanilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 597039083-(Nonafluorobutane-1-sulfonyloxy)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester

Produkt 1

HCID 59703874
3-(4-Bromo-2-fluoro-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester
Ausbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A degassed solution of 3-(nonafluorobutane-1-sulfonyloxy)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester (422 mg, 0.83 mmol), 4bromo -2-fluoroaniline (206 mg, 1.08 mmol), Pd2 dba3 (38 mg, 0.04 mmol), Xantphos (48 mg, 0.08 mmol) and DBU (316 μl, 2.08 mmol) in toluene (1 ml) was subjected to microwave irradiation at 150° C. for 10 minutes. The reaction mixture was cooled to ambient temperature then diluted with ethyl acetate (30 ml). The resultant solution was washed with water (20 ml), dried over sodium sulfate and concentrated in vacuo to give a solid residue. The solid residue was purified by flash chromatography (Si-SPE, pentane:diethyl ether, gradient 90:10 to 70:30) to afford the title compound as a white solid (210 mg, 64%). LCMS (method B): RT=3.78 min, M+H+=395/397.

Aufarbeitung

  1. customirradiation at 150° C. for 10 minutes
  2. washThe resultant solution was washed with water (20 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a solid residue
  6. customThe solid residue was purified by flash chromatography (Si-SPE, pentane:diethyl ether, gradient 90:10 to 70:30)

Quellen und Nachweise

ORD-Eintrag
ord-543dd4da60c8452d87acf4577df6922c
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07893085B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion