Potassium Carbonate → 6-(3,5-Difluorophenyl)-5'-methylspiro[chroman-4,2'-imidazol]-4'-amine

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Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]2[C:11]3([N:15]=[C:14]([NH2:16])[C:13]([CH3:17])=[N:12]3)[CH2:10][CH2:9][O:8][C:5]2=[CH:6][CH:7]=1.[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[C:23]([F:25])[CH:24]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:18][C:19]1[CH:20]=[C:21]([C:2]2[CH:3]=[C:4]3[C:11]4([N:15]=[C:14]([NH2:16])[C:13]([CH3:17])=[N:12]4)[CH2:10][CH2:9][O:8][C:5]3=[CH:6][CH:7]=2)[CH:22]=[C:23]([F:25])[CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

6-Bromo-5′-methylspiro[chroman-4,2′-imidazol]-4′-amine (Intermediate 4, 0.10 g, 0.34 mmol), 3,5-difluorophenylboronic acid (0.11 g, 0.68 mmol) and 2M K2CO3 (aq., 0.34 mL, 0.69 mmol) were mixed in dioxane (3 mL) and degassed by passing through nitrogen for 5 min. Then (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (14 mg, 20 μmol) was added and the mixture was heated in a microwave oven at 130° C. for 1 h. Purification by preparative chromatography gave the title compound (17 mg, 15% yield): 1H NMR (400 MHz, CDCl3) δ ppm 2.25 (m, 2 H), 2.41 (s, 3 H), 4.57 (m, 2 H), 6.66-6.86 (m, 2 H), 6.89-7.05 (m, 3 H), 7.38 (d, 1 H), 8.1-9.0 (br m, 2 H); MS (ES+) m/z 328 [M+H]+.

Aufarbeitung

customdegassed
customPurification by preparative chromatography

Quellen und Nachweise

ORD-Eintrag: ord-2d6f8b5413ee4ead84895db93fbadf63
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08865911B2

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