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Benzo[b]furan-2-boronic acid → Tert-butyl 2'-(2-(benzofuran-2-yl)pyrimidin-4-yl)-5'-(4-methoxybenzyl)-4'-oxo-1',4',5',6'-tetrahydrospiro[piperidine-4,7'-pyrrolo [3,2-c]pyridine]-1-carboxylate

HRID 513097
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 513097
Cl[C:2]1[N:7]=[C:6]([C:8]2[NH:16][C:15]3[C:14]4([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]4)[CH2:13][N:12]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)[C:11](=[O:38])[C:10]=3[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[O:39]1[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[CH:41]=[C:40]1B(O)O>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[O:39]1[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[CH:41]=[C:40]1[C:2]1[N:7]=[C:6]([C:8]2[NH:16][C:15]3[C:14]4([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]4)[CH2:13][N:12]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)[C:11](=[O:38])[C:10]=3[CH:9]=2)[CH:5]=[CH:4][N:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 2776266Benzo[b]furan-2-boronic acidHCID 86671415HCID 86671415, Verbindung

Produkt 1

HCID 68315015Tert-butyl 2'-(2-(benzofuran-2-yl)pyrimidin-4-yl)-5'-(4-methoxybenzyl)-4'-oxo-1',4',5',6'-tetrahydrospiro[piperidine-4,7'-pyrrolo [3,2-c]pyridine]-1-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of tert-butyl 2′-(2-chloropyrimidin-4-yl)-5′-(4-methoxybenzyl)-4′-oxo-1′,4′,5′,6′-tetrahydrospiro[piperidine-4,7′-pyrrolo[3,2-c]pyridine]-1-carboxylate (A5) (4.5 g, 8.36 mmol), 2-benzofuranboronic acid (4.06 g, 25.09 mmol) and potassium phosphate tribasic heptahydrate (8.49 g, 25.09 mmol) was dissolved in anhydrous dioxane (105 mL). The resulting solution was purged with nitrogen, followed by addition of 1,1′-bis(diphenylphosphino)ferrocene palladium(II)chloride (676 mg, 0.836 mmol). The resulting mixture was again purged with nitrogen and stirred at 140° C. for 45 min in the microwave. After cooling to room temperature, the reaction mixture was diluted with EtOAc, washed three times with aqueous NaHCO3, once with brine, dried over Na2SO4, filtered and concentrated under vacuum. The crude product was triturated with toluene which gave tert-butyl 2′-(2-(benzofuran-2-yl)pyrimidin-4-yl)-5′-(4-methoxybenzyl)-4′-oxo-1′,4′,5′,6′-tetrahydrospiro[piperidine-4,7′-pyrrolo[3,2-c]pyridine]-1-carboxylate (A6) as a white solid (3.60 g, 70%). 1H NMR (400 MHz, DMSO-D6, 300K): δ=1.42 (9H, s), 1.55 (2H, br d, J=13.0 Hz), 2.08 (2H, br dt, J=13.4 Hz), 2.65 (2H, br s), 3.56 (2H, br s), 3.74 (3H, s), 3.80 (2H, br s), 4.57 (2H, br s), 6.92 (2H, d, J=8.6 Hz), 7.31 (2H, d, J=8.6 Hz), 7.35 (1H, t, J=7.6 Hz), 7.43 (1H, s), 7.46 (1H, t, J=7.8 Hz), 7.75 (1H, d, J=8.2 Hz), 7.80 (1H, d, J=5.5 Hz), 7.82 (1H, d, J=7.7 Hz), 8.03 (1H, s), 8.77 (1H, d, J=5.4 Hz), 11.75 (1H, s). MS (ES) C36H37N5O5 requires: 619. found: 620.2 [M+H]+.

Aufarbeitung

  1. customThe resulting solution was purged with nitrogen
  2. customThe resulting mixture was again purged with nitrogen
  3. temperatureAfter cooling to room temperature
  4. additionthe reaction mixture was diluted with EtOAc
  5. washwashed three times with aqueous NaHCO3
  6. dry with materialonce with brine, dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude product was triturated with toluene which

Quellen und Nachweise

ORD-Eintrag
ord-8e0a59ea549943bc8a9d00f6a632fd0a
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09102676B2

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