Water → 2-(6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

HRID 245865

Reaktionsgleichung

Reaktionsgleichung von HRID 245865
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][C:10]=2[Sn](CCCC)(CCCC)CCCC)[CH:7]=1.Br[C:25]1[N:26]=[C:27]2[C:33]([CH:34]=[O:35])=[CH:32][N:31]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[C:28]2=[N:29][CH:30]=1.O>CN(C=O)C.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.[Cu]I>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][C:10]=2[C:25]2[N:26]=[C:27]3[C:33]([CH:34]=[O:35])=[CH:32][N:31]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[C:28]3=[N:29][CH:30]=2)[CH:7]=1

Komponenten

7

Edukt 3

HCID 962WaterHCID 578296122-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehydeHCID 712799216-Fluoro-1-tributylstannyl-imidazo[1,5-a]pyridine

Produkt 1

HCID 866779082-(6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehydeAusbeute 105,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a round-bottomed flask, 6-fluoro-1-tributylstannyl-imidazo[1,5-a]pyridine (577 mg, 0.81 mmol) and 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (210 mg, 0.59 mmol) were dissolved in DMF (5 ml). The flask was evacuated and backfilled with argon then tetrakis(triphenylphosphine)palladium (0) (33 mg, 0.029 mmol) and copper (I) iodide (22 mg, 0.12 mmol) were added. The reaction mixture was stirred at 80° C. in an oil bath for 4 h then cooled to room temperature. Water was added and the resulting suspension was filtered. The filter cake was washed with water and petroleum ether then dried under high vacuum to afford 256 mg (95%) of 2-(6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde as a yellow powder.

Aufarbeitung

  1. customThe flask was evacuated
  2. temperaturethen cooled to room temperature
  3. filtrationthe resulting suspension was filtered
  4. washThe filter cake was washed with water and petroleum ether
  5. customthen dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8bb9ce7c10bf490d962e7b5c7c4af8e1
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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