Reaktion #78265

Reaktionsgleichung

(S)-2-(3,5-dichloro-phenyl)-10,10a-dihydro-5H-imidazo[1,5-b]isoquinoline-1,3-dione

4-bromobenzyl bromide

→

compound

Ausbeute 66.8%

10a-(4-Bromo-benzyl)-2-(3,5-dichloro-phenyl)-10,10a-dihydro-5H-imidazo[1,5-b]isoquinoline-1,3-dione

Ausbeute 66.8%

Lösungsmittel

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred at −50 C
2. 2
   workup.WAITfor 30 min.
3. 3
   Temperaturto warm to RT
4. 4
   workup.STIRRINGstirred overnight
5. 5
   Sonstigepartitioned between brine and t-Bu methyl ether
6. 6
   TrocknenThe organic layer was dried over MgSO4
7. 7
   Einengenconcentrated in vacuo
8. 8
   Sonstigethe residue purified by HPLC

Vorschrift

To a solution of (S)-2-(3,5-dichloro-phenyl)-10,10a-dihydro-5H-imidazo[1,5-b]isoquinoline-1,3-dione (100 mg) (0.1 mmol) (Prep. 22) in 2.5 mL of dry THF at −40° C. was added a 1 M solution of LIHMDS (0.5 mL) in THF. The reaction mixture was stirred for 15 min. at −40° C. and a solution of 4-bromobenzyl bromide (70 mg) in 1 mL of dry THF was added. The reaction mixture was stirred at −50 C. for 30 min., allowed to warm to RT, stirred overnight, then partitioned between brine and t-Bu methyl ether. The organic layer was dried over MgSO4, concentrated in vacuo, and the residue purified by HPLC to afford the above compound (34.5 mg). NMR (CDCl3, 200 MHz): 7.45 (2H, d), 7.25-7.35 (5H, m), 6.95-7.0 (4H, d+d), 5.15 (1H, d), 4.55 (1H, d), 3.25 (2H, s), 3.20 (1H, d), 2.95 (1H, d).

Quelle