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Water → tert-Butyl 2-(6-formylpyridin-2-yl)benzyl(phenyl)carbamate

HRID 1944834
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1944834
O.C(=O)([O-])[O-].[Na+].[Na+].Br[C:9]1[N:14]=[C:13]([CH:15]=[O:16])[CH:12]=[CH:11][CH:10]=1.[C:17]1([N:23]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2B2OC(C)(C)C(C)(C)O2)[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1.O.CO.CO>[CH:15]([C:13]1[N:14]=[C:9]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[CH2:31][N:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:10]=[CH:11][CH:12]=1)=[O:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27570096-Bromopyridine-2-carbaldehydeHCID 66795645Tert-butyl phenyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate

Produkt 1

HCID 58434438tert-Butyl 2-(6-formylpyridin-2-yl)benzyl(phenyl)carbamateAusbeute 840 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel2×HCID 22242641Methanol--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of water (160 mL) and methanol (40 mL) was combined with sodium carbonate (3.80 g, 35.9 mmol), and the mixture was sparged with nitrogen for 30 min. In a separate flask were combined, under nitrogen, 6-bromo-2-pyridinecarboxaldehyde (2.67 g, 14.4 mmol), tert-butyl phenyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate (5.87 g, 14.4 mmol), tetrakis(triphenylphosphinio)palladium (0.829 g, 0.718 mmol), and toluene (150 mL). The water-methanol solution was added via cannula to the toluene solution, and the biphasic mixture was heated to 80° C. overnight. At this time 1H NMR spectroscopic analysis of an aliquot indicated that the reaction was complete. The clear yellow organic layer was separated, dried with brine, then over magnesium sulfate. The crude product was purified by chromatography on silica using 1:1 hexanes:dichloromethane elutant and increasing the strength by addition of up to 10% EtOAc. The product was isolated as a sticky oil (4.7 g, 840%). 1H NMR (CD2Cl2, 500 MHz): 10.0 (s, 1H), 7.83-7.92 (m, 2H), 7.56 (d, 1H), 7.50 (d, 1H), 7.44 (m, 1H), 7.36 (m, 2H), 7.17 (t, 2H), 7.01 (t, 1H), 7.0 (br d, 2H), 5.11 (s, 2H), 1.34 (s, 9H).

Aufarbeitung

  1. customthe mixture was sparged with nitrogen for 30 min
  2. customIn a separate flask were combined, under nitrogen
  3. customThe clear yellow organic layer was separated
  4. dry with materialdried with brine
  5. customThe crude product was purified by chromatography on silica using 1:1 hexanes
  6. temperaturedichloromethane elutant and increasing the strength
  7. additionby addition of up to 10% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-44db1aceaade4a65ad7630d6644dabf9
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08394902B2

Notizen zur Reaktion

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