1-(Benzyloxy)-3-bromobenzene → 2-Methyl-1-(3-phenylmethoxyphenyl)-6-(trifluoromethoxy)indole
Reaction equation
Brc1cccc(OCc2ccccc2)c1.Cc1cc2ccc(OC(F)(F)F)cc2[nH]1>CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C.CC(C)(C)[O-].Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd]>Cc1cc2ccc(OC(F)(F)F)cc2n1-c1cccc(OCc2ccccc2)c1Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
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.
Sources & evidence
- ORD record
- ord-0addbbece6dc4ca2acdd8d8c9131d423
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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