Sodium Carbonate → (1R,3S)-methyl 3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-1-methylcyclohexanecarboxylate

HRID 527028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527028
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C@@:11]([CH3:19])([C:15]([O:17][CH3:18])=[O:16])[CH2:10]2)[C:5]([F:20])=[CH:4][N:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]2[C:30](B3OC(C)(C)C(C)(C)O3)=[CH:29][N:28]([S:40]([C:43]3[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=3)(=[O:42])=[O:41])[C:25]2=[N:26][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O>[Cl:21][C:22]1[CH:23]=[C:24]2[C:30]([C:2]3[N:7]=[C:6]([NH:8][C@H:9]4[CH2:14][CH2:13][CH2:12][C@@:11]([CH3:19])([C:15]([O:17][CH3:18])=[O:16])[CH2:10]4)[C:5]([F:20])=[CH:4][N:3]=3)=[CH:29][N:28]([S:40]([C:43]3[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=3)(=[O:41])=[O:42])[C:25]2=[N:26][CH:27]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 575977475-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 86667436(1R,3S)-methyl 3-(2-chloro-5-fluoropyrimidin-4-ylamino)-1-methylcyclohexanecarboxylate2×

Produkt 1

HCID 68008233(1R,3S)-methyl 3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-1-methylcyclohexanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a 25 mL round-bottomed flask were combined (1R,3S)-methyl 3-(2-chloro-5-fluoropyrimidin-4-ylamino)-1-methylcyclohexanecarboxylate, 52h, (0.061 g, 0.202 mmol), 5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine (0.096 g, 0.222 mmol), disodium carbonate (0.064 g, 0.607 mmol) in 5 mL of THF and 1 ml of water. The reaction mixture was degassed via a stream of nitrogen. To the reaction was added tetrakis triphenyl phosphine palladium (0) (0.021 g, 0.202 mmol) and the reaction was stirred at reflux overnight. The reaction was concentrated in vacuo and purified by silica gel chromatography (4:1 Hexanes:EtOAc), yielding 85 mg of desired product, 52i.

Aufarbeitung

  1. customIn a 25 mL round-bottomed flask were combined
  2. customThe reaction mixture was degassed via a stream of nitrogen
  3. temperatureat reflux overnight
  4. concentrationThe reaction was concentrated in vacuo
  5. custompurified by silica gel chromatography (4:1 Hexanes:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-81a6949858644d25809cb65f09a601fa
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345708B2

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