Reaktion #525

ord-0addbbece6dc4ca2acdd8d8c9131d423

Reaktionsgleichung

Brc1cccc(OCc2ccccc2)c1
Brc1cccc(OCc2ccccc2)
Cc1cc2ccc(OC(F)(F)F)cc2[nH]1
Cc1cc2ccc(OC(F)(F)F)
→
Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1
Cc1cc2ccc(OC(F)(F)F)
Ausbeute 59.1%

Edukte

Brc1cccc(OCc2ccccc2)c1
Brc1cccc(OCc2ccccc2)c1
Cc1cc2ccc(OC(F)(F)F)cc2[nH]1
Cc1cc2ccc(OC(F)(F)F)cc2[nH]1

Reagenzien

CC(C)(C)[O-].[Na+]
CC(C)(C)[O-].[Na+]
CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C
CC(C)(C)P(c1ccccc1-c1ccccc1)C(
O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]
O=C(/C=C/c1ccccc1)/C=C/c1ccccc

Lösungsmittel

Cc1ccccc1
Cc1ccccc1

Reaktionsbedingungen

Temperatur
100°CELSIUS

Vorschrift

EN04773-53, _Buchwald coupling, toluene and bromide_ The indole from 4773-25, 1-(benzyloxy)-3-bromobenzene,Pd2(dba)3, JohnPhos and KOtBu were dissolved in toluene. The mixture was warmed at 100 °C for 2h. Ca 60% conversion according to LCMS (product at 2.31 min). This conversion rate seemed faster than for the corresponding aryliodide. Big bacth was performed in 4773-54.

Quelle

750 AstraZeneca ELN dataset