Reaktion #167963

Reaktionsgleichung

(R)-1-(4-(6-benzyl-2-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)ethanone

3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indole

Na2CO3

→

(R)-1-(4-(6-benzyl-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)ethanone

Lösungsmittel

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed
2. 2
   Sonstigeby sparging with argon
3. 3
   FiltrationThe reaction was filtered
4. 4
   workup.ADDITIONdiluted with EtOAc
5. 5
   Waschenwashed successively with sat aq Na2CO3 and, brine
6. 6
   Trocknendried over Na2SO4
7. 7
   EinengenAfter concentration the residue
8. 8
   Sonstigewas purified by FCC (5-70% EtOAc/heptane)

Vorschrift

A mixture of (R)-1-(4-(6-benzyl-2-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)ethanone (0.27 g, 0.675 mmol), 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indole (0.305 g, 0.743 mmol) and 2 M aq Na2CO3 (1.1 mL, 2.19 mmol) in DME (3 mL) was degassed by sparging with argon. Pd(PPh3P)4 (0.117 g, 0.101 mmol) was then added and the mixture was heated in a microwave reactor at 140° C. for 1.5 h. The reaction was filtered and diluted with EtOAc, washed successively with sat aq Na2CO3 and, brine, and then dried over Na2SO4. After concentration the residue was purified by FCC (5-70% EtOAc/heptane) to provide (R)-1-(4-(6-benzyl-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)ethanone. MS (ESI+) m/z 649.3 (M+H)+.

Quelle