Sodium Bicarbonate → 2-(5-{7-[2-(1-Boc-pyrrolidin-2-yl)-3H-imidazol-4-yl]-9,10-dihydro-phenanthren-2-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 417396

Reaktionsgleichung

Reaktionsgleichung von HRID 417396
CC1(C)C(C)(C)OB([C:9]2[CH:22]=[CH:21][C:20]3[C:19]4[C:14](=[CH:15][C:16](B5OC(C)(C)C(C)(C)O5)=[CH:17][CH:18]=4)[CH2:13][CH2:12][C:11]=3[CH:10]=2)O1.[C:33]([O:37][C:38]([N:40]1[CH2:44][CH2:43][CH2:42][CH:41]1[C:45]1[NH:46][CH:47]=[C:48](Br)[N:49]=1)=[O:39])([CH3:36])([CH3:35])[CH3:34].[C:51]([O-:54])(O)=[O:52].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:33]([O:37][C:38]([N:40]1[CH2:44][CH2:43][CH2:42][CH:41]1[C:45]1[NH:49][C:48]([C:9]2[CH:10]=[CH:11][C:20]3[C:19]4[C:14](=[CH:15][C:16]([C:48]5[NH:49][C:45]([CH:41]6[CH2:42][CH2:43][CH2:44][N:40]6[C:51]([O:54][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:52])=[N:46][CH:47]=5)=[CH:17][CH:18]=4)[CH2:13][CH2:12][C:21]=3[CH:22]=2)=[CH:47][N:46]=1)=[O:39])([CH3:36])([CH3:35])[CH3:34]

Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 587894764,4,5,5-Tetramethyl-2-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9,10-dihydro-phenanthren-2-yl]-[1,3,2]dioxaborolaneHCID 178451675HCID 178451675, Verbindung

Produkt 1

HCID 666212102-(5-{7-[2-(1-Boc-pyrrolidin-2-yl)-3H-imidazol-4-yl]-9,10-dihydro-phenanthren-2-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Pd(PPh3)4 (31 mg, 0.03 mmol) was added to a mixture 4,4,5,5-tetramethyl-2-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9,10-dihydro-phenanthren-2-yl]-[1,3,2]dioxaborolane (115 mg, 0.27 mmol), 2-(4-bromo-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (173 mg, 0.55 mmol), NaHCO3 (159 mg, 1.9 mmol) in 1,2-dimethoxyethane (5 mL) and water (1 mL). The reaction mixture was flushed with nitrogen, heated at 80° C. for 6 hours, and then the volatile component was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product as a white solid (42 mg, 24%). m/z 651.0 (M+H)+.

Aufarbeitung

  1. customThe reaction mixture was flushed with nitrogen
  2. customthe volatile component was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  4. washwashed with NaHCO3 solution, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe obtained residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-68e399114b9742249fdbf56a000e55ec
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088368B2

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