Reaktion #1586206

Reaktionsgleichung

9

(2-Chloro-4-morpholin-4-yl-pyrido[3′,2′:4,5]furo[3,2-d]pyrimidin-8-ylmethyl)-dimethyl-amine

indole-4-boronic acid

Na2CO3

dioxane

→

[2-(1H-Indol-4-yl)-4-morpholin-4-yl-pyrido[3′,2′:4,5]furo[3,2-d]pyrimidin-8-ylmethyl]-dimethyl-amine

Lösungsmittel

water

EtOAc

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe lid was sealed
2. 2
   Temperaturwas cooled to rt
3. 3
   SonstigeThe organic layer was separated
4. 4
   Extraktionthe aqueous layer extracted with EtOAc (2×10 mL)
5. 5
   TrocknenThe combined organic layers were then dried (MgSO4)
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigePurification by flash column chromatography on silica (eluant 2-5% MeOH/CH2Cl2)
8. 8
   Sonstigefurnished H (2 mg, 0.005 mmol, 32%) as an off-white solid

Vorschrift

To a sealed tube was added 9 (5 mg, 0.014 mmol), indole-4-boronic acid (5.8 mg, 0.036 mmol), dichloro-bis(triphenylphosphine)palladium (II) (2.0mg, 0.0029 mmol) and Na2CO3 (3.1 mg, 0.029 mmol) followed by dioxane (2 mL) and water (0.8 mL) under Ar(g). The lid was sealed and the tube was heated to 88° C. for 18 h whereupon it was cooled to rt and diluted with EtOAc (35 mL) and 50% saturated brine (5 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×10 mL). The combined organic layers were then dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography on silica (eluant 2-5% MeOH/CH2Cl2) furnished H (2 mg, 0.005 mmol, 32%) as an off-white solid.

Quelle