N-bromobutanimide → 1-[3-(4-Bromo-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)-urea

HRID 407515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 407515
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([C:21]2[NH:22][N:23]=[CH:24][CH:25]=2)[CH:14]=1)=[O:11].[Br:26]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C>[Br:26][C:25]1[CH:24]=[N:23][NH:22][C:21]=1[C:15]1[CH:14]=[C:13]([NH:12][C:10]([NH:9][C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])=[O:11])[CH:18]=[CH:17][C:16]=1[O:19][CH3:20]

Komponenten

5

Edukt 3

HCID 67184N-bromobutanimideHCID 22607107sodium thiosulfate NaHCO3HCID 231394671-(2,4-Difluoro-phenyl)-3-[4-methoxy-3-(2H-pyrazol-3-yl)-phenyl]-urea

Produkt 1

HCID 231395161-[3-(4-Bromo-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)-ureaAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a cooled and stirred solution of 1-(2,4-Difluoro-phenyl)-3-[4-methoxy-3-(2H-pyrazol-3-yl)-phenyl]-urea (0.6 g, 1.74 mmole) in DMF (15 mL) was added N-bromosuccinimide (0.37 g, 2.09 mmole) over a period of 15 minutes. The reaction mixture was warmed slowly to ambient temperature and stirred for another 2 hrs. The reaction mixture was poured into well-stirred ice water containing NaHCO3/Na2S2O3. The resulting solid was filtered and washed with ice water (50 mL). The solid was dried in vacuo to afford off-white solid (0.68 g, 92%). LCMS m/z (%)=425 (M+H, 79Br, 100), 427 (M+H, 81 Br, 99). 1H NMR (Bruker, 400 MHz, DMSO-d6) δ: 8.96 (bs, 1H), 8.44 (bs, 1H), 8.02-8.08 (m, 1H), 7.48 (bs, 2H), 7.27-7.32 (m, 1 h), 6.99-7.08 (m, 2H), 3.73 (s, 3H) (major tautomer).

Aufarbeitung

  1. temperatureTo a cooled
  2. additionThe reaction mixture was poured
  3. filtrationThe resulting solid was filtered
  4. washwashed with ice water (50 mL)
  5. customThe solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6dc3edadd95e4afda40da783e86c2486
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754238B2

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