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Sodium Carbonate → 4-(8-Tert-butoxycarbonylamino-6-oxo-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-2-yl)-3,6-dihydro-2h-pyridine-1-carboxylic acid tert-butyl ester

HRID 2375110
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2375110
C([O-])([O-])=O.[Na+].[Na+].COC([C:11]1[NH:12][C:13]2[CH:14]=[C:15]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:16]=[C:17]3[C:23](=[O:24])[NH:22][N:21]=[CH:20][C:19]=1[C:18]=23)=O.[C:33]([O:37][C:38]([N:40]1[CH2:45][CH:44]=[C:43](B2OC(C)(C)C(C)(C)O2)[CH2:42][CH2:41]1)=[O:39])([CH3:36])([CH3:35])[CH3:34]>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:33]([O:37][C:38]([N:40]1[CH2:41][CH:42]=[C:43]([C:11]2[NH:12][C:13]3[CH:14]=[C:15]([NH:25][C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH:16]=[C:17]4[C:23](=[O:24])[NH:22][N:21]=[CH:20][C:19]=2[C:18]=34)[CH2:44][CH2:45]1)=[O:39])([CH3:36])([CH3:34])[CH3:35]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 1361816128-tert-Butoxycarbonylamino-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indole-2-carboxylic acid methyl ester

Produkt 1

HCID 1361816454-(8-Tert-butoxycarbonylamino-6-oxo-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-2-yl)-3,6-dihydro-2h-pyridine-1-carboxylic acid tert-butyl ester
Ausbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Under an argon atmosphere, 2.0 M aqueous Na2CO3 (0.66 mL) was added to a mixture of Intermediate 147(d) of Example 147 (100 mg, 0.265 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (122 mg, 0.395 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (10.8 mg, 0.013 mmol) in anhydrous N,N-dimethylformamide (5 ml). The mixture was heated at 80° C. for 16 hours. The reaction was filtered through a thin pack of diatomaceous earth, and the volatile components were removed in vacuo. Silica gel chromatography (eluted with 1:1 ethyl acetate:hexane) afforded the title compound (120 mg, 0.249 mmol) as a yellow powder in 94% yield.

Aufarbeitung

  1. filtrationThe reaction was filtered through a thin pack of diatomaceous earth
  2. customthe volatile components were removed in vacuo
  3. washSilica gel chromatography (eluted with 1:1 ethyl acetate:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0a0b1faec240401c9842aa89131aa1a1
Quelldatensatz
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07462713B2

Notizen zur Reaktion

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