7-Chloro-2-iodothieno(3,2-b)pyridine → 6-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

HRID 1676393Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676393
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14](=[O:15])[N:13]3[CH2:16][CH2:17][N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:12]3=[N:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Cl[C:26]1[CH:31]=[CH:30][N:29]=[C:28]2[CH:32]=[C:33]([I:35])[S:34][C:27]=12>CN(C1C=CN=CC=1)C.BrC1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14](=[O:15])[N:13]3[CH2:16][CH2:17][N:18]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:12]3=[N:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:26]1[CH:31]=[CH:30][N:29]=[C:28]2[CH:32]=[C:33]([I:35])[S:34][C:27]=12

Komponenten

5

Edukt 2

HCID 177504007-Chloro-2-iodothieno(3,2-b)pyridineHCID 673463376-(3-fluoro-4-hydroxyphenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

Produkt 1

HCID 673468456-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 7961BromobenzeneLösungsmittel

Versuchsvorschrift

A mixture of 6-(3-fluoro-4-hydroxyphenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one (0.078 g, 0.186 mmol), 7-chloro-2-iodothieno[3,2-b]pyridine (0.050 g, 0.169 mmol; prepared according to the procedure of Ragan, J. A. Org. Proc. Res. 2003, 7, 676) and DMAP (0.021 g, 0.169 mmol) in bromobenzene (1.5 mL) under nitrogen was stirred at 150° C. for two days. The reaction was concentrated in vacuo to remove as much bromobenzene as possible and then purified directly by flash column chromatography, eluting with 30:1 CH2Cl2/MeOH. The product was obtained (35 mg; 36%) as a yellow solid. LRMS (APCI pos) m/e 583 (M+1).

Aufarbeitung

  1. customprepared
  2. concentrationThe reaction was concentrated in vacuo
  3. customto remove as much bromobenzene as possible and
  4. customthen purified directly by flash column chromatography
  5. washeluting with 30:1 CH2Cl2/MeOH
  6. customThe product was obtained (35 mg; 36%) as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-b91f38f2304e41f59d98ac96f778fc51
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003662B2

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