Sodium Hydroxide → HCID 11177187, Verbindung

HRID 2192291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192291
[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-imidazo[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-96081e3055bb4552824fcc082f5eea5d
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329727B2

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