Cesium carbonate → N-(2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl)cyclopropanecarboxamide

HRID 626654

Reaktionsgleichung

Reaktionsgleichung von HRID 626654
Cl[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[CH:5]=[CH:4][N:3]=1.[CH:19]1([C:22]([NH2:24])=[O:23])[CH2:21][CH2:20]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:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[N:9]1[CH:8]=[C:7]2[C:2]([NH:24][C:22]([CH:19]3[CH2:21][CH2:20]3)=[O:23])=[N:3][CH:4]=[CH:5][C:6]2=[N:10]1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 80376CyclopropanecarboxamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866970364-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

Produkt 1

HCID 69671224N-(2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl)cyclopropanecarboxamideAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

A suspension of 4-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (25 mg, 0.084 mmol), cyclopropanecarboxamide (16 mg, 0.19 mmol), Xantphos (14 mg, 0.024 mmol), Pd2(dba)3 (14 mg, 0.016 mmol) and Cs2CO3 (152 mg, 0.470 mmol) in dry dioxane (4.0 mL) was sealed in a microwave vial after degassing with nitrogen. The mixture was irradiated at 160° C. for 60 minutes in the microwave and then cooled to room temperature. The solid material was removed via filtration and the filtrate was purified via prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to afford N-(2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl)cyclopropanecarboxamide (10 mg, 35% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.19 (br, 1H), 8.90 (s, 1H), 7.99 (d, J=6.5 Hz, 1H), 7.79-7.67 (m, 3H), 7.39 (d, J=6.0 Hz, 1H), 2.13 (m, 1H), 0.92-0.86 (m, 4H). LCMS (Method A): RT=5.50 min, m/z: 347.0 [M+H+].

Aufarbeitung

  1. customwas sealed in a microwave vial
  2. customafter degassing with nitrogen
  3. customThe mixture was irradiated at 160° C. for 60 minutes in the microwave
  4. customThe solid material was removed via filtration
  5. customthe filtrate was purified via 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-785056e2441a4315af3de8ec18e8ec64
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309240B2

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