1,4-Dioxane → 4-((2-Chloro-5-(2-methylbenzo[d]oxazol-6-yl)-7-((2-(trimethylsilyl)ethoxy)-methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-1-methylcyclohexanol

HRID 1487618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1487618
[Cl:1][C:2]1[N:3]=[C:4]([O:20][CH:21]2[CH2:26][CH2:25][C:24]([CH3:28])([OH:27])[CH2:23][CH2:22]2)[C:5]2[C:10](I)=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[N:7]=1.[CH3:29][C:30]1[O:31][C:32]2[CH:38]=[C:37](B3OC(C)(C)C(C)(C)O3)[CH:36]=[CH:35][C:33]=2[N:34]=1.O.O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>O>[Cl:1][C:2]1[N:3]=[C:4]([O:20][CH:21]2[CH2:26][CH2:25][C:24]([CH3:28])([OH:27])[CH2:23][CH2:22]2)[C:5]2[C:10]([C:37]3[CH:36]=[CH:35][C:33]4[N:34]=[C:30]([CH3:29])[O:31][C:32]=4[CH:38]=3)=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[N:7]=1

Komponenten

6

Edukt 4

HCID 312751,4-DioxaneHCID 18407952Tripotassium phosphate trihydrateHCID 709750612-Methyl-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzoxazoleHCID 867264454-((2-Chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-1-methylcyclohexanol

Produkt 1

HCID 867264464-((2-Chloro-5-(2-methylbenzo[d]oxazol-6-yl)-7-((2-(trimethylsilyl)ethoxy)-methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-1-methylcyclohexanolAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a degassed mixture of 4-((2-chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-1-methylcyclohexanol (1 equiv), 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (1.2 equiv) and tripotassium phosphate trihydrate (3 equiv) in a 9:1 mixture of 1,4-dioxane and water (0.18 M) was added palladium 1,1-bis(diphenylphosphion)ferrocene dichloride (0.1 equiv). The reaction mixture was stirred at 70° C. for 3 h. After the reaction was completed, the reaction mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (0-2% DCM in MeOH) to afford the title compound (95% yield) as a red oil. MS (ESI) m/z 543.2 [M+1]+.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (0-2% DCM in MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-f9e24ccc96d74268ae14a88ea36184f3
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428509B2

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