Thiourea → 4-(4-Fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-ylamine

HRID 2108736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2108736
Br[CH2:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[F:14])[NH:7][CH:6]=1)=O.[NH2:15][C:16]([NH2:18])=[S:17]>C(O)C>[F:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]2[NH:7][CH:6]=[C:5]([C:3]3[N:15]=[C:16]([NH2:18])[S:17][CH:2]=3)[C:13]=12

Komponenten

4

Edukt 2

HCID 2723790ThioureaHCID 57421973Ethanone, 2-bromo-1-(4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-

Produkt 1

HCID 576331034-(4-Fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-ylamineAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To an ethanol suspension of 2-bromo-1-(4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone (3.00 g 0.0117 mol) was added thiourea (1.18 g, 0.0234 mol), the reaction mixture was heated at 70° C. for 1 h. The suspension was filtered while still warm and to the filtration cake was added sat. sodium carbonate solution until the aqueous phase pH was around 7.5. The suspension was filtered to afford 1.8 g free base (75%). H NMR, DMSO-d6: 6.78 (s, 1H), 6.9 (s, br, 2H), 6.98 (m, 1H), 7.71 (s, 1H), 8.25 (m, 1H).

Aufarbeitung

  1. filtrationThe suspension was filtered
  2. temperaturewhile still warm and to the filtration cake
  3. additionwas added sat. sodium carbonate solution until the aqueous phase pH was around 7.5
  4. filtrationThe suspension was filtered

Quellen und Nachweise

ORD-Eintrag
ord-3097e10220934020a7dc21d448e293ee
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514448B2

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