Reaktion #70315

ord-d30981efe9454498b823b5946518673b

Reaktionsgleichung

COC(=O)c1cc(Br)ccc1N
methyl 2-amino-5-bromobenzoate
OB(O)C1CC1
cyclopropylboronic acid
O=P([O-])([O-])[O-].[K+].[K+].[K+]
K3PO4
C1CCC(P(C2CCCCC2)C2CCCCC2)CC1
P(Cy)3
COC(=O)c1cc(C2CC2)ccc1N
expected product
Ausbeute 88.3%
COC(=O)c1cc(C2CC2)ccc1N
Methyl 2-amino-5-cyclopropylbenzoate
Ausbeute 88.3%

Lösungsmittel

Reaktionsbedingungen

Temperatur
100°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe reaction mixture was filtered through celite
  2. 2
    Sonstigethe organic phase was separated
  3. 3
    Sonstigeevaporated

Vorschrift

In a schlenck tube, a mixture of methyl 2-amino-5-bromobenzoate (43.47 mmol, 10 g), cyclopropylboronic acid (112.92 mmol, 9.700 g), K3PO4 (144.16 mmol, 30.6 g), Pd (AcO)2 (3.47 mmol, 0.780 g), P(Cy)3 (7.85 mmol, 2.2 g) in toluene (170 ml) and water (10 ml) was heated for 2 hours at 100° C., under nitrogen atmosphere. The reaction mixture was filtered through celite and the organic phase was separated and evaporated affording 7.34 g (yield 77%) of the expected product.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536165B2uspto-grants-2013_09