Cesium carbonate → HCID 67128656, Verbindung

HRID 449920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449920
Br[C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:20])[C:10]2[C:15]([Cl:16])=[CH:14][C:13]([CH:17]=[CH2:18])=[CH:12][C:11]=2[Cl:19])[CH:5]=[CH:4][N:3]=1.[CH:21]1([C:24]([NH2:26])=[O:25])[CH2:23][CH2:22]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.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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]>[Cl:19][C:11]1[CH:12]=[C:13]([CH:17]=[CH2:18])[CH:14]=[C:15]([Cl:16])[C:10]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:26][C:24]([CH:21]2[CH2:23][CH2:22]2)=[O:25])[CH:7]=1)=[O:20]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 80376CyclopropanecarboxamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86648960N-(2-bromopyridin-4-yl)-2,6-dichloro-4-vinylbenzamide

Produkt 1

HCID 67128656HCID 67128656, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of N-(2-bromopyridin-4-yl)-2,6-dichloro-4-vinylbenzamide (23 mg, 0.062 mmol), cyclopropanecarboxamide (16 mg, 0.19 mmol), Pd2(dba)3 (6.0 mg, 0.0062 mmol), Xantphos (7.0 mg, 0.012 mmol) and Cs2CO3 (40 mg, 0.12 mmol) in dioxane (2 mL) was heated to 140° C. for 1 hour in a microwave reactor under nitrogen atmosphere. The mixture was filtered through Celite and concentrated under reduced pressure. The residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to afford 2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-vinylbenzamide (10 mg, yield: 43%). 1H NMR (500 MHz, CDCl3): δ 8.26 (s, 1H), 7.99-7.97 (m, 2H), 7.74 (s, 1H), 7.37 (s, 2H), 6.64 (m, 1H), 5.86 (m, 1H), 5.47 (m, 1H), 1.52 (m, 1H), 1.09-1.05 (m, 2H), 0.92-0.88 (m, 2H). LCMS (ESI) m/z: 376.1 [M+H+].

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min)

Quellen und Nachweise

ORD-Eintrag
ord-522e6c80ba504f2fb1e9ccb2e5a38b3b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486950B2

Notizen zur Reaktion

Wird geladen…