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

HRID 539317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539317
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.[Cl:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[C:23]([Cl: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]>[Cl: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]([Cl:25])[CH:24]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27343313,5-Dichlorophenylboronic acidHCID 679796056-Bromo-5'-methylspiro[chromane-4,2'-imidazol]-4'-amine2×

Produkt 1

HCID 573846146-(3,5-Dichlorophenyl)-5'-methylspiro[chroman-4,2'-imidazol]-4'-amineAusbeute 14,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

6-Bromo-5′-methylspiro[chroman-4,2′-imidazol]-4′-amine (73 mg, 0.25 mmol, Intermediate 4), 3,5-dichlorophenylboronic acid (95 mg, 0.50 mmol) and K2CO3 (83 mg, 0.60 mmol) were mixed in dioxane (2 mL) and degassed by passing nitrogen through for 5 min. Then (1,1′-bis(diphenyl-phosphino)ferrocene)-dichloropalladium(II) (10 mg, 0.01 mmol) was added and the mixture was heated in a sealed vial at 100° C. overnight. (1,1′-Bis(diphenylphosphino)ferrocene)-dichloro-palladium(II) (10 mg, 0.01 mmol) was added and heating continued in a microwave oven at 130° C. for 2×1 h. Purification by preparative HPLC gave the title compound (13 mg, 14% yield): 1H NMR (400 MHz, CDCl3) δ ppm 2.04-2.30 (m, 2 H), 2.38 (s, 3 H), 4.50-4.69 (m, 2 H), 4.88 (br s, 2 H), 6.69 (s, 1 H), 6.98 (d, 1 H), 7.22-7.35 (m, 4 H); MS (ES+) m/z 360 [M+H]+.

Aufarbeitung

  1. customdegassed
  2. customthrough for 5 min
  3. temperatureheating
  4. customcontinued in a microwave oven at 130° C. for 2×1 h
  5. customPurification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-1ebccceb30094b9f971273ecd3ff2187
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865911B2

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