Phenolate → tert-butyl 4-(2-(4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-1H-imidazol-1-yl)ethyl)piperazine-1-carboxylate

HRID 1400918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400918
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.CC([O-])(C)C.[K+].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]2[CH:23]=[C:24]([C:26]3[N:27]=[CH:28][N:29]([CH2:31][CH2:32][N:33]4[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]4)[CH:30]=3)[S:25][C:18]=12.Cl.NC1C=CC(O)=C(F)C=1.C1([O-])C=CC=CC=1>CN1C(=O)CCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[CH:23]=[C:24]([C:26]4[N:27]=[CH:28][N:29]([CH2:31][CH2:32][N:33]5[CH2:34][CH2:35][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:37][CH2:38]5)[CH:30]=4)[S:25][C:18]=23)=[C:4]([F:9])[CH:3]=1

Komponenten

7

Edukt 5

HCID 119047PhenolateHCID 2735918Phenol, 4-amino-2-fluoro-HCID 195992014-Amino-2-fluorophenol hydrochlorideHCID 23665647Potassium tert-butoxide2×HCID 67442621tert-butyl 4-(2-(4-(7-chlorothieno[3,2-b]pyridin-2-yl)-1H-imidazol-1-yl)ethyl)piperazine-1-carboxylate

Produkt 1

HCID 67442156tert-butyl 4-(2-(4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-1H-imidazol-1-yl)ethyl)piperazine-1-carboxylateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred solution of 4-amino-2-fluorophenol x HCl (1.64 g, 10.05 mmol) in NMP (30 mL) was added t-BuOK (2.25 g, 20.1 mmol). After 30 min, compound 305 (3.75 g, 8.37 mmol) was added and the reaction mixture was heated at 100° C. for 1 h. A solution of 4-amino-2-fluorophenol HCl (1.64 g, 10.05 mmol) in NMP (30 mL) in a separate flask was treated with t-BuOK (2.25 g, 20.1 mmol) and the resultant phenolate solution was added to the reaction mixture at 100° C. After 30 min, the reaction was quenched by addition of water and the precipitate was collected by filtration, dried and triturated with MTBE to afford the title compound 306 (2.10 g, 3.90 mmol, 47% yield) as a beige solid. MS (m/z): 539.39 (M+H).

Aufarbeitung

  1. waitAfter 30 min
  2. customthe reaction was quenched by addition of water
  3. filtrationthe precipitate was collected by filtration
  4. customdried
  5. customtriturated with MTBE

Quellen und Nachweise

ORD-Eintrag
ord-adfe92d5b6324b769324c96a74dca69d
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906852B2

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