Sodium Bicarbonate → (S)-tert-butyl 4-(4-(1-acetyl-2-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)benzoyl)piperazine-1-carboxylate

HRID 1485753Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1485753
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:14])[CH3:13])[C@@H:7]([CH3:15])[CH2:6][NH:5]2.CC1(C)C(C)(C)OB([C:24]2[CH:44]=[CH:43][C:27]([C:28]([N:30]3[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]3)=[O:29])=[CH:26][CH:25]=2)O1.C(=O)(O)[O-].[Na+]>O1CCOCC1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:12]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([C:24]3[CH:44]=[CH:43][C:27]([C:28]([N:30]4[CH2:31][CH2:32][N:33]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH2:34][CH2:35]4)=[O:29])=[CH:26][CH:25]=3)=[CH:11][CH:10]=2)[NH:5][CH2:6][C@@H:7]1[CH3:15])(=[O:14])[CH3:13]

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 17749917(4-(4-BOC-piperazine-1-carbonyl)phenyl)boronic acid pinacol esterHCID 118078861(S)-1-(6-bromo-2-methyl-3,4-dihydroquinoxalin-1(2H)-yl)ethanone

Produkt 1

HCID 118079960(S)-tert-butyl 4-(4-(1-acetyl-2-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)benzoyl)piperazine-1-carboxylateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419050HCID 178419050, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of (S)-1-(6-bromo-2-methyl-3,4-dihydroquinoxaline-1(2H)-yl)ethanone (0.200 g, 0.743 mmol), tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl)piperazine-1-carboxylate (0.340 g, 0.817 mmol), bis(triphenylphosphine)palladium (II) dichloride (0.052 g, 0.074 mmol), and sodium bicarbonate (1 M in water, 1.5 mL, 1.5 mmol) in 1,4-dioxane (3.7 mL) was heated at 80° C. for 16 h. The reaction mixture was filtered through Celite and concentrated to afford an orange oil. This material was purified via column chromatography on silica gel (gradient elution with 0-100% ethyl acetate-hexane) to afford (S)-tert-butyl 4-(4-(1-acetyl-2-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)benzoyl)piperazine-1-carboxylate (0.294 g, 83%) as an off-white solid. MS (ESI, pos. ion) m/z 479.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated
  3. customto afford an orange oil
  4. customThis material was purified via column chromatography on silica gel (gradient elution with 0-100% ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e42b6be38fcf4445828ec1a617153f07
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422281B2

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