Sodium Hydroxide → HCID 11177187, Verbindung

HRID 1992531Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1992531
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:16][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][C:10]=2[N:9]=1.[OH-].[Na+].Cl[CH2:20][C:21]1[O:25][N:24]=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH:22]=1>CN(C=O)C>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([C:23]2[CH:22]=[C:21]([CH2:20][N:13]3[CH:14]=[CH:15][C:10]4=[N:9][C:8]([C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=5[F:1])=[N:16][C:11]4=[CH:12]3)[O:25][N:24]=2)=[CH:31][CH:30]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 27640565-(Chloromethyl)-3-(4-chlorophenyl)-1,2-oxazoleHCID 134507782-(2-Fluorophenyl)-3H-imidazo[4,5-c]pyridine

Produkt 1

HCID 11177187HCID 11177187, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of 2-(2-fluorophenyl)-3H-imidazo[4,5-c]pyridine (11.0 g, 50.0 mmoles) in DMF was added a 10% (w/v) solution of aqueous NaOH. To this solution, 5-(chloromethyl)-3-(4-chlorophenyl)isoxazole (13.68 g, 60.0 mmoles) dissolved in DMF was added. The reaction mixture was stirred at room temperature and monitored every half hour by LCMS. The reaction was stopped at 4 hours, after LCMS showed no progress between at 2 hour and 4 hour monitor points. The reaction product was triturated with first with water and then with EtoAc (3×). The material was crystallized by dissolving the material in MeOH with heat, followed by precipitation with water. This crystallization process was then repeated yielding 5-((3-(4-chlorophenyl)isoxazol-5-yl)methyl)-2-(2-fluorophenyl)-5H-imdazo[4,5-c]pyridine (15.385 g, 38 mmole) as white crystal at a yield of 74%. 1H 300 Mhz (d6-DMSO) sigma 6.02 (s, 2p); 7.13 (s, 1p); 7.26-7.35 (m, 2p); 7.43-7.52 (m, 1p); 7.56 (d, 2p); 7.84 (d, 1); 7.89 (d, 2p); 8.24 (d, 1); 8.28-8.36 (m, 1p); and 9.19 (s, 1p). LCMS data M/Z=405.31

Aufarbeitung

  1. additionwas added
  2. waitThe reaction was stopped at 4 hours
  3. custombetween at 2 hour and 4 hour monitor points
  4. customThe reaction product was triturated with first with water
  5. customThe material was crystallized
  6. dissolutionby dissolving the material in MeOH
  7. temperaturewith heat
  8. customfollowed by precipitation with water

Quellen und Nachweise

ORD-Eintrag
ord-237fdfe97b764955861d0594856c6860
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07648998B2

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