Dimethylformamide → 5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

HRID 246562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246562
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:9][N:8](COCC[Si](C)(C)C)[C:5]2=[N:6][CH:7]=1.ClC1C=C2C(C([Sn](CCCC)(CCCC)CCCC)=NN2C)=CC=1.CN(C=[O:54])C>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:54][CH2:17][C:14]([NH:13][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[CH:2][N:3]=2)[NH:8][CH:9]=1)=[O:12])([CH3:15])[CH3:16]

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 712805996-chloro-1-methyl-3-tributylstannanyl-1H-indazoleHCID 715756452-bromo-N-(tert-butyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Produkt 1

HCID 866779905H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amideAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-Bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (90 mg, 0.203 mmol) and 6-chloro-1-methyl-3-(tributylstannyl)-1H-indazole (0.148 g, 0.228 mmol) were dissolved in DMF (3 mL). The reaction mixture was evacuated and filled with nitrogen then copper(I) iodide (9 mg, 0.081 mmol) and tetrakis(triphenylphosphine)palladium (0) (46 mg, 0.046 mmol) were added. The reaction mixture was heated at 90° C. for 2 h then partitioned between ethyl acetate and water. The organic phase was washed with brine then dried over magnesium sulfate. The crude material was purified by chromatography using 25% ethyl acetate/hexane to obtain 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-trimethyl-silanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (40 mg, 37%).

Aufarbeitung

  1. customThe reaction mixture was evacuated
  2. additionfilled with nitrogen
  3. customthen partitioned between ethyl acetate and water
  4. washThe organic phase was washed with brine
  5. dry with materialthen dried over magnesium sulfate
  6. customThe crude material was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3ed928d963664bd997d27383d055c715
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

Notizen zur Reaktion

Wird geladen…