Sodium Bicarbonate → tert-butyl 4-(4-(5-fluoro-2-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)piperidine-1-carboxylate

HRID 527989

Reaktionsgleichung

Reaktionsgleichung von HRID 527989
Cl[C:2]1[C:3]2[CH:10]=[C:9]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)(O)[O-].[Na+].[F:29][C:30]1[CH:31]=[CH:32][C:33]([O:39][CH3:40])=[C:34](B(O)O)[CH:35]=1>CN(C)C=O.O.C(OCC)(=O)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.[Cl-].[Cl-].[Fe+2].[Pd+2]>[F:29][C:30]1[CH:35]=[CH:34][C:33]([O:39][CH3:40])=[C:32]([C:2]2[C:3]3[CH:10]=[C:9]([CH:11]4[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]4)[NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:31]=1

Komponenten

8

Edukt 3

HCID 516892Sodium BicarbonateHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 90418107tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)piperidine-1-carboxylate

Produkt 1

HCID 90418838tert-butyl 4-(4-(5-fluoro-2-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 53384307Dichloro[1,1'-bis(di-tert-butylphosphino)ferrocene]palladium(II)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of Example 1C (200 mg, 0.6 mmol) in N,N-dimethylformamide (8 mL), was added a solution of sodium bicarbonate (0.118 g, 1.404 mmol) in 0.5 mL water followed by 5-fluoro-2-methoxyphenylboronic acid (204 mg, 1.2 mmol). The mixture was degassed with nitrogen and [1,1′-bis(di tert butyl phosphino)ferrocene]palladium(II) dichloride (21 mg, 0.033 mmol) was added. The mixture was heated under microwave conditions (Biotage Initiator) at 100° C. for 1 hour. The mixture was diluted with ethyl acetate and filtered through diatomaceous earth. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, concentrated and purified by column chromatography (silica gel, 40% ethyl acetate-hexane) to afford the title compound. LCMS: 427.21 (M+1)+.

Aufarbeitung

  1. additionwas added
  2. filtrationfiltered through diatomaceous earth
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography (silica gel, 40% ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8b01117117ae4def8e3a9bfba393835a
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346813B2

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