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Ethanol → (2'-Amino-biphenyl-3-yl)-acetic acid methyl ester

HRID 383602
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 383602
N#N.C(O)C.[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1B(O)O.[CH3:16][O:17][C:18](=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22](Br)[CH:21]=1>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:16][O:17][C:18](=[O:27])[CH2:19][C:20]1[CH:25]=[C:24]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH2:6])[CH:23]=[CH:22][CH:21]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 702EthanolHCID 947NitrogenHCID 2773216(2-Aminophenyl)boronic acidHCID 11746402Methyl 2-(3-bromophenyl)acetate

Produkt 1

HCID 16116037(2'-Amino-biphenyl-3-yl)-acetic acid methyl esterAusbeute 106,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

(The following reaction is done in an oxygenfree N2 atmosphere.) Add ethanol (0.8 mL), Tetrakis-(triphenylphosphine)-palladium(0) (30 mg, 2.2 mol %) and Na2CO3 decahydrate (944 mg, 3.30 mmol; presolved in 1.2 mL H2O) subsequently to dissolved 2-Amino-benzeneboronic acid (70) (201 mg, 1.30 mmol) in toluene (6.0 mL). Degas the reaction mixture for 5 times and flood with N2 again. Add (3-Bromo-phenyl)-acetic acid methyl ester (69) (270 mg, 1.18 mmol) in toluene (6.0 mL), degas again (5 times) and stir the reaction solution overnight at 100° C. Partition the reaction solution between EtOAc and brine (1+1) and extract the separated aqueous layer 3 times with EtOAc. Wash combined organic layer with brine and dry with Na2SO4. Remove solvent under reduced pressure and purify the crude product by preparative radial chromatography (silica gel 60 PF, CyH/EtOAc 3+1) to obtain (2′-Amino-biphenyl-3-yl)-acetic acid methyl ester (71) as an orange oil (304 mg, 81%). 1H NMR (400 MHz, CDCl3): 3.66 (s, 2H); 3.69 (s, 3H); 3.62-3.86 (br.s, 2H); 6.75 (d, 1H, J=8.1 Hz); 6.80 (t, 1H, J=7.3 Hz); 7.11 (d, 1 H, J=7.3 Hz); 7.15 (d, 1H, J=8.1 Hz); 7.22-7.26 (br.m, 1H); 7.32-7.42 (m, 3H).

Aufarbeitung

  1. custom(The following reaction
  2. customDegas the reaction mixture for 5 times and flood with N2 again
  3. customPartition the reaction solution between EtOAc and brine (1+1)
  4. extractionextract the separated aqueous layer 3 times with EtOAc
  5. washWash
  6. dry with materialdry with Na2SO4
  7. customRemove solvent under reduced pressure and purify the crude product by preparative radial chromatography (silica gel 60 PF, CyH/EtOAc 3+1)

Quellen und Nachweise

ORD-Eintrag
ord-2e00f144eb2a42b98629dc467dee78b7
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08367677B2

Notizen zur Reaktion

Wird geladen…

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