Triethylamine → 3-[5-Bromo-2-(3-fluoro-benzyloxy)-phenoxy]-1-tert-butyl-azetidine

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Reaktionsgleichung

[C:1]([N:5]1[CH2:8][CH:7]([OH:9])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(OCl)(=O)=O.[Br:23][C:24]1[CH:25]=[CH:26][C:27]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)=[C:28](O)[CH:29]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)=[C:26]([CH:25]=1)[O:9][CH:7]1[CH2:8][N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6]1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

To a solution of the title compound of Step A (3 mmol), and triethylamine (6 mmol) in CH2Cl2 (50 mL), was added MeSO3Cl (4 mmol). The mixture was stirred at 25° C. for 16 h. After concentration, ⅓ of the residue was dissolved in MeCN (20 mL). Next, 5-bromo-2-(3-fluoro-benzyloxy)-phenol (0.5 mmol) and K2CO3 (2 mmol) were added. The mixture was stirred at 100° C. for 16 h, concentrated and purified via PTLC providing the title compound (189 mg). MS (ESI): mass calcd. for C20H23BrFNO2, 407.1; m/z found, 408.0 [M+H]+. 1H NMR (CDCl3): 7.37-7.28 (m, 1H), 7.19-7.12 (m, 2H), 7.04-6.95 (m, 2H), 6.84-6.63 (m, 2H), 5.08 (s, 2H), 4.78-4.48 (m, 1H), 3.68-3.62 (m, 2H), 3.35-3.26 (m, 2H), 1.00 (s, 9H).

Aufarbeitung

concentrationAfter concentration, ⅓ of the residue
dissolutionwas dissolved in MeCN (20 mL)
stirringThe mixture was stirred at 100° C. for 16 h
concentrationconcentrated
custompurified via PTLC

Quellen und Nachweise

ORD-Eintrag: ord-aa6463d549f84e12a53050ba26241be7
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08642583B2

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