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2-bromo-N-(tert-butyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide → 2-(5-difluoromethoxy-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

HRID 246297
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 246297
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14](Br)[N:15]=2)[N:10]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:26][CH:27]([F:51])[O:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][N:33]=[C:32]2[Sn](CCCC)(CCCC)CCCC>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>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:32]3[C:31]4[C:35](=[CH:36][CH:37]=[C:29]([O:28][CH:27]([F:26])[F:51])[CH:30]=4)[NH:34][N:33]=3)[N:15]=2)[N:10]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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Komponenten

6

Edukt 2

HCID 715756452-bromo-N-(tert-butyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideHCID 1784482315-(difluoromethoxy)-3-(tributylstannyl)-1H-indazole

Produkt 1

HCID 712795662-(5-difluoromethoxy-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamideAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

In a round-bottomed flask, 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (200 mg, 0.47 mmol) and 5-difluoromethoxy-3-tributylstannyl-1H-indazole (crude from Step 1, 509 mg, 0.59 mmol) were dissolved in DMF (3.2 ml). The reaction mixture was evacuated and backfilled with argon then tetrakis(triphenylphosphine)palladium (0) (27.0 mg, 0.023 mmol) and copper (I) iodide (18 mg, 0.095 mmol) were added. The reaction mixture was stirred at 90° C. for 2 h then cooled to room temperature, quenched with water and extracted with ethyl acetate/diethyl ether (2×). The combined organic layers were washed three times with water and once with brine then concentrated. The residue was absorbed on silica gel and chromatographed with EtOAc/dichloromethane (gradient: 0-30% EtOAc). The appropriate fractions were combined and concentrated and the residue was triturated with diethyl ether to afford 158 mg (64%) of 2-(5-difluoromethoxy-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as an off-white powder.

Aufarbeitung

  1. customThe reaction mixture was evacuated
  2. temperaturethen cooled to room temperature
  3. customquenched with water
  4. extractionextracted with ethyl acetate/diethyl ether (2×)
  5. washThe combined organic layers were washed three times with water
  6. concentrationonce with brine then concentrated
  7. customThe residue was absorbed on silica gel
  8. customchromatographed with EtOAc/dichloromethane (gradient: 0-30% EtOAc)
  9. concentrationconcentrated
  10. customthe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-db2b0b77c3d74fc59dc9f8afc0cd40e1
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658646B2

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