Sodium Carbonate → HCID 131734996, Verbindung

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Reaktionsgleichung

[C:1]([O:5][C:6](=[O:34])[N:7]([CH:9]([C:11](=[O:33])[NH:12][C:13]1[CH:18]=[C:17](Br)[C:16]([Cl:20])=[C:15]([C:21]#[C:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[N:14]=1)[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:35][N:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][C:43]=2B(O)O)[CH:38]=[N:37]1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[C:1]([O:5][C:6](=[O:34])[N:7]([C@H:9]([C:11](=[O:33])[NH:12][C:13]1[CH:18]=[C:17]([C:43]2[CH:42]=[CH:41][CH:40]=[C:39]3[C:44]=2[N:36]([CH3:35])[N:37]=[CH:38]3)[C:16]([Cl:20])=[C:15]([C:21]#[C:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[N:14]=1)[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (20 mg, 0.03 mmol) is added to a mixture of tert-butyl-N-{1-[(4-bromo-5-chloro-6-{2-[tris(propan-2-yl)silyl]ethynyl}-pyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamate C2 (82 mg, 0.14 mmol), (1-methyl-1H-indazol-7-yl)boronic acid (24 mg, 0.14 mmol), Na2CO3 (44 mg, 0.42 mmol), dioxane (0.8 ml) and water (0.2 ml) under argon atmosphere and stirred at 100° C. for 4 h. The mixture is diluted with water (10 ml) and extracted with EtOAc. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 25 mg (28%). HPLC-MS: M+H=624; tR=1.94 min (METHOD—1).

Aufarbeitung

extractionextracted with EtOAc
dry with materialThe combined organic layers are dried over MgSO4
concentrationconcentrated in vacuo
customThe product is purified by RP HPLC

Quellen und Nachweise

ORD-Eintrag: ord-1c681887f67341188b475b9338c8185f
Quelldatensatz: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09278978B2

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