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tert-Butyl acrylate → (E)-Benzyl 4-(4-(3-tert-butoxy-3-oxoprop-1-enyl)-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

HRID 528924
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 528924
Br[C:2]1[C:3]([C:36](=[O:46])[N:37]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:38][CH2:39][CH2:40][CH3:41])=[N:4][N:5]([C:8]2[CH:23]=[CH:22][C:11]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[CH:10][C:9]=2[C:24]([N:26]2[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27]2)=[O:25])[C:6]=1[CH3:7].[C:47]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])(=[O:50])[CH:48]=[CH2:49]>CN(C=O)C.CCN(CC)CC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:52]([O:51][C:47](=[O:50])/[CH:48]=[CH:49]/[C:2]1[C:3]([C:36](=[O:46])[N:37]([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:42][CH2:43][CH2:44][CH3:45])=[N:4][N:5]([C:8]2[CH:23]=[CH:22][C:11]([C:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])=[CH:10][C:9]=2[C:24]([N:26]2[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27]2)=[O:25])[C:6]=1[CH3:7])([CH3:55])([CH3:54])[CH3:53]
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Komponenten

6

Edukt 2

HCID 15458tert-Butyl acrylateHCID 71062156Benzyl 4-(4-bromo-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate2×

Produkt 1

HCID 71062592(E)-Benzyl 4-(4-(3-tert-butoxy-3-oxoprop-1-enyl)-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 6228DimethylformamideLösungsmittel
HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of benzyl 4-(4-bromo-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (Intermediate 164A, 80 mg, 0.12 mmol) in DMF (580 μL) and Et3N (580 μL) was added (PPh3)2PdCl2 (8 mg, 0.012 mmol) followed by tert-butyl acrylate (58 μL, 0.40 mmol). The reaction mixture was purged with N2 for 5 min and then heated at 140° C. overnight. The reaction mixture was poured into a separatory funnel containing 1N aq. HCl solution and EtOAc. The organic layer was washed 1N aq. HCl solution (2×) and the aqueous layer was extracted with EtOAc (3×). The combined organic extracts were washed with sat. aq. NaHCO3 solution, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (gradient from 0% to 35% EtOAc/hexanes) to provide the title compound (42 mg, 50%) as a colorless oil. MS(ESI+) m/z 733.5 (M+H)+.

Aufarbeitung

  1. customThe reaction mixture was purged with N2 for 5 min
  2. additionThe reaction mixture was poured into a separatory funnel
  3. additioncontaining 1N aq. HCl solution and EtOAc
  4. washThe organic layer was washed 1N aq. HCl solution (2×)
  5. extractionthe aqueous layer was extracted with EtOAc (3×)
  6. washThe combined organic extracts were washed with sat. aq. NaHCO3 solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (gradient from 0% to 35% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8a7293510f9c4e6c91071d013ed97a7b
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09346795B2

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