Reaktion #680801

Reaktionsgleichung

N-(5-bromo-pyridin-3-ylmethyl)-methanesulfonamide

N-Boc-6-chloro-indole-2-boronic acid

s-Phos

potassium phosphate

→

6-chloro-2-[5-(methanesulfonylamino-methyl)-pyridin-3-yl]-indole-1-carboxylic acid tert-butyl ester

Lösungsmittel

toluene

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture is degassed for 15 min
2. 2
   TemperaturThe mixture is cooled to room temperature
3. 3
   workup.ADDITIONis added
4. 4
   EinengenThe mixture is concentrated in vacuo
5. 5
   Sonstigethe residue is purified by silica gel flash chromatography
6. 6
   Wascheneluting with a 0 to 90% ethyl acetate-heptane gradient

Vorschrift

A flask is charged with N-(5-bromo-pyridin-3-ylmethyl)-methanesulfonamide (Example 163a, 530 mg, 2 mmol), N-Boc-6-chloro-indole-2-boronic acid (525 mg, 3.0 mmol), s-Phos (41 mg, 0.10 mmol), finely crushed potassium phosphate (849 mg, 4.0 mmol) and toluene (20 mL), and the mixture is degassed for 15 min. Pd2dba3 (37 mg, 0.04 mmol) is added and the mixture is stirred at 85° C. for 1 h. The mixture is cooled to room temperature, diluted with DCM and silica gel (10 g) is added. The mixture is concentrated in vacuo and the residue is purified by silica gel flash chromatography eluting with a 0 to 90% ethyl acetate-heptane gradient to give 6-chloro-2-[5-(methanesulfonylamino-methyl)-pyridin-3-yl]-indole-1-carboxylic acid tert-butyl ester. MS (ESI) m/z 436.1 and 437.9 (M+H)+.

Quelle