Sodium Carbonate → HCID 178427348, Verbindung

HRID 527081

Reaktionsgleichung

Reaktionsgleichung von HRID 527081
[C:1]([O:5][C:6]([NH:8][C:9](=[N:26]C(=O)OC(C)(C)C)[NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18]2[C:23]([F:24])=[CH:22][N:21]=[C:20](Cl)[N:19]=2)[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:34][C:35]1[CH:36]=[C:37]2[C:43](B3OC(C)(C)C(C)(C)O3)=[CH:42][N:41]([S:53]([C:56]3[CH:61]=[CH:60][C:59]([CH3:62])=[CH:58][CH:57]=3)(=[O:55])=[O:54])[C:38]2=[N:39][CH:40]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:24][C:23]1[C:18]([NH:17][C@H:13]2[CH2:14][CH2:15][CH2:16][C@@H:11]([NH:10][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[NH:26])[CH2:12]2)=[N:19][C:20]([C:43]2[C:37]3[C:38](=[N:39][CH:40]=[C:35]([F:34])[CH:36]=3)[N:41]([S:53]([C:56]3[CH:61]=[CH:60][C:59]([CH3:62])=[CH:58][CH:57]=3)(=[O:54])=[O:55])[CH:42]=2)=[N:21][CH:22]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 672856905-fluoro-1-((4-methylphenyl)sulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 178454306HCID 178454306, Verbindung

Produkt 1

HCID 178427348HCID 178427348, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 15220664Palladium--triphenylphosphane (1/1)KatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Degassed a solution of (Z)-tert-butyl (tert-butoxycarbonylamino) ((1R,3S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexylamino)methylenecarbamate, 70b, (0.200 g, 0.411 mmol), 5-fluoro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine, 44a, (0.205 g, 0.493 mmol) and Na2CO3 (0.616 mL of 2M solution, 1.232 mmol) in dimethoxyethane (15 mL) for 30 min. To the mixture was added palladium triphenylphosphane (0.023 g, 0.021 mmol) and the reaction mixture was heated in a pressure tube at 120° C. for 45 min. The reaction mixture was filtered through a pad of celite and the filtrate concentrated in vacuo. Attempted purification of the resulting residue by silica gel chromatography (10% MeOH/CH2Cl2) yielded a mixture containing mostly desired product that was used without further purification: LCMS RT=2.30 (M+H) 641.02.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customAttempted purification of the resulting residue by silica gel chromatography (10% MeOH/CH2Cl2)
  4. customyielded a mixture

Quellen und Nachweise

ORD-Eintrag
ord-d5f0b8e0275e494ea94050bdb7d0b2ae
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345708B2

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