Dimethylformamide → N-tert-butyl-2-(6-fluoro-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246634
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([Sn](CCCC)(CCCC)CCCC)=[N:7][NH:8]2)=[CH:4][CH:3]=1.Br[C:25]1[N:26]=[C:27]2[C:33]([C:34]([NH:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[CH:32][NH:31][C:28]2=[N:29][CH:30]=1.CN(C=O)C>O.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)I>[C:37]([NH:36][C:34]([C:33]1[C:27]2[C:28](=[N:29][CH:30]=[C:25]([C:6]3[C:5]4[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=4)[NH:8][N:7]=3)[N:26]=2)[NH:31][CH:32]=1)=[O:35])([CH3:40])([CH3:38])[CH3:39]

Komponenten

7

Edukt 3

HCID 6228DimethylformamideHCID 866779952-bromo-N-tert-butyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideHCID 1784482326-fluoro-3-(tributylstannyl)-1H-indazole

Produkt 1

HCID 71280703N-tert-butyl-2-(6-fluoro-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

The mixture of 6-fluoro-3-(tributylstannyl)-1H-indazole (500 mg, 1.17 mmol), 2-bromo-N-tert-butyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (258 mg, 0.9 mmol), tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol), copper iodide (10 mg 0.052 mmol) in 15 ml, of dry DMF was heated to 90° C. for 2.5 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature, diluted with 50 mL of water and filtered. The solid was washed with dichloromethane and hot methanol, then filtered to give N-tert-butyl-2-(6-fluoro-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide as a yellow solid (260 mg, 82%). 1H NMR (300 MHz, DMSO): δ 13.82 (s, 1H), 12.96 (s, 1H), 9.10 (s, 1H), 8.48-8.43 (m, 1H), 8.33 (s, 1H), 7.92 (s, 1H), 7.44-7.41 (m, 1H), 7.12-7.06 (m, 1H), 3.14 (d, 1H, J=5.1 Hz), 1.51 (s, 9H). LCMS: 353.0, [M+H]+.

Aufarbeitung

  1. filtrationfiltered
  2. washThe solid was washed with dichloromethane and hot methanol
  3. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-f300aba324764bb09dc2209c58a16789
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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