Sodium Carbonate → N-tert-butyl-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246664Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246664
Br[C:2]1[N:7]=[C:6]2[C:8]([C:11]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:9][NH:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[CH:28][CH:29]=[C:30]3[C:34]=2[N:33]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[N:32]=[CH:31]3)O1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:14]([NH:13][C:11]([C:8]1[C:6]2=[N:7][C:2]([C:26]3[CH:27]=[CH:28][CH:29]=[C:30]4[C:34]=3[N:33]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[N:32]=[CH:31]4)=[CH:3][N:4]=[C:5]2[NH:10][CH:9]=1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 712800667-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazoleHCID 866779952-bromo-N-tert-butyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Produkt 1

HCID 71280304N-tert-butyl-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamideAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2-bromo-N-tert-butyl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (0.1 g, 0.337 mmol), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (121 mg, 0.37 mmol), Pd2(dba)3 (39 mg, 0.067 mmol), X-Phos (64 mg, 0.135 mmol) and Na2CO3 (107 mg, 1.01 mmol) in dioxane (20 mL) and water (5 mL) was heated to 90° C. for 16 hours under N2 atmosphere. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate (20 mL) and water (10 mL), organic phase was washed with brine (10 mL) then dried over Na2SO4 and concentrated to afford N-tert-butyl-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (120 mg, crude) as yellow oil. LCMS: (M+H)+=465.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate (20 mL) and water (10 mL), organic phase
  3. washwas washed with brine (10 mL)
  4. dry with materialthen dried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-db63391edcff48818962a226d54c5f68
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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