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1,3-Dibromo-5,5-dimethylhydantoin → HCID 178467426, Verbindung

HRID 1852891
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1852891
[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH:9]([CH:11]2[CH2:14][CH2:13][CH2:12]2)[CH3:10])[C:5]2[N:15]([CH2:18][C@H:19]3[CH2:24][CH2:23][C@H:22]([CH3:25])[CH2:21][CH2:20]3)[CH:16]=[N:17][C:4]=2[CH:3]=1.[Cl-].[Li+].CC1(C)CCCC(C)(C)N1[Mg]Cl.[Br:40]N1C(C)(C)C(=O)N(Br)C1=O>C1COCC1>[Br:40][C:16]1[N:15]([CH2:18][C@H:19]2[CH2:20][CH2:21][C@H:22]([CH3:25])[CH2:23][CH2:24]2)[C:5]2[C:6]([O:8][CH:9]([CH:11]3[CH2:12][CH2:13][CH2:14]3)[CH3:10])=[N:7][C:2]([Cl:1])=[CH:3][C:4]=2[N:17]=1
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Komponenten

5

Edukt 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 178424953HCID 178424953, VerbindungHCID 178467428HCID 178467428, Verbindung

Produkt 1

HCID 178467426HCID 178467426, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 6-chloro-4-(1-cyclobutylethoxy)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine (3.5 g, 11.73 mmol) in THF (20 mL) was added 2,2,6,6-tetramethylpiperidinyl magnesium chloride lithium chloride complex (1.0 M in THF/Toluene, 29.8 mL, 29.84 mmol) at −78° C. The resulting solution was stirred 2.5 hours and then 1,3 dibromo-5,5 dimethyl hydantoin (8.5 g, 29.84 mmol) in THF (20 mL) was added dropwise at −78° C. The reaction was stirred for 30 minutes then slowly warmed to room temperature over a period of 2 hours. The reaction was quenched with saturated NH4Cl solution (50 mL) at 0° C. and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography (eluting with 8-10% EtOAc/petroleum ether) to yield 2-bromo-6-chloro-4-(1-cyclobutylethoxy)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine. MS ES/APCI calc'd. for C20H27BrClN3O [M+H]+ 440. found 440.

Aufarbeitung

  1. stirringThe reaction was stirred for 30 minutes
  2. customThe reaction was quenched with saturated NH4Cl solution (50 mL) at 0° C.
  3. extractionextracted with EtOAc (2×20 mL)
  4. washThe combined organic extracts were washed with water (20 mL) and brine (20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (eluting with 8-10% EtOAc/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-6d6f5b4461c3476ebee8798b95b24eba
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08962611B2

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