Potassium Phosphate, Tribasic → [5-Cyclopropyl-2-(3-hexyl-phenyl)-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 545378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 545378
[CH2:1]([C:7]1[CH:8]=[C:9]([C:13]2[N:17]([CH3:18])[C:16]([C:19]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[CH2:23][CH2:22]3)=[O:20])=[C:15](I)[N:14]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH:33]1(B(O)O)[CH2:35][CH2:34]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:33]1([C:15]2[N:14]=[C:13]([C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:8]=3)[N:17]([CH3:18])[C:16]=2[C:19]([N:21]2[CH2:22][CH2:23][CH:24]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:25][CH2:26]2)=[O:20])[CH2:35][CH2:34]1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 57541122[2-(3-Hexyl-phenyl)-5-iodo-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Produkt 1

HCID 57541173[5-Cyclopropyl-2-(3-hexyl-phenyl)-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanoneAusbeute 33,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of 0.275 g (0.50 mmol) of [2-(3-hexyl-phenyl)-5-iodo-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 2), 0.086 g (1.0 mmol) of cyclopropyl boronic acid and 0.573 g (2.7 mmol) of tribasic potassium phosphate in 10 ml of toluene was treated with 0.30 ml of water, followed by 0.031 g (0.11 mmol) of tricyclohexylphosphine and 0.012 g (0.055 mmol) of palladium(II)acetate. This reaction mixture was heated up to 100° C., stirred for 18 hours at this temperature and subsequently cooled down to RT. The reaction mixture was then poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1) to give 0.077 g (33%) of the title compound as light yellow oil. MS: 463.4 (MH+).

Aufarbeitung

  1. temperaturesubsequently cooled down to RT
  2. additionThe reaction mixture was then poured
  3. extractionextracted twice with EtOAc
  4. washthe organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-d3b657b313ab477483b1025b3ce9fb97
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935707B2

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