Reaktion #44455

Reaktionsgleichung

(1-Ethoxyvinyl)tributyl tin

trans-N-(7-bromo-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

HCl

→

title compound

Ausbeute 47.0%

trans-N-(7-Acetyl-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

Ausbeute 47.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   workup.STIRRINGthe reaction mixture was stirred for 1 h
3. 3
   SonstigeThe reaction was quenched with sat NaHCO3 (aq)
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe organic layer was washed with brine
6. 6
   Trocknendried (Na2SO4)
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe crude compound was chromatographed with heptane/ethyl acetate 1:1

Vorschrift

(1-Ethoxyvinyl)tributyl tin (90 μl, 0.23 mmol) was added to a solution of trans-N-(7-bromo-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (100 mg, 0.23 mmol) and PdCl2(PPh3)2 (3 mg, 4.3 μmol) in toluene (6 mL) under N2. The reaction mixture was heated to 140° C. and stirred for 3 h. After cooling to room temperature, 2N (aq) HCl (450 ul) was added and the reaction mixture was stirred for 1 h. The reaction was quenched with sat NaHCO3 (aq) and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and evaporated. The crude compound was chromatographed with heptane/ethyl acetate 1:1. Purifcation by HPLC gave the title compound (43 mg, 47%). Data: 1H-NMR (400 MHz, DMSO) 1.60-2.09 (m, 4H), 3.21 (t, J=11.2, 1H), 3.90 (d, J=14.0, 1H), 4.16 (d, J=10.4, 1H), 4.44 (m, 1H), 7.04-7.54 (m, 10H), 9.20 (d, J=10.0, 1H). (m/z)=405 (M+H)+.

Quelle