5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide → Biphenyl

HRID 608931Notes

Reaction equation

HRID 608931 reaction equation
CN(C)C(=NC(C)(C)C)N(C)C.Cc1cc(O)ccc1B1OC(C)(C)C(C)(C)O1.O=C(NCc1ccc(F)cc1)c1nc(Br)c2cccnc2c1O>CC(C)(C)[PH](C(C)(C)C)(C(C)(C)C)[Pd]1([Cl])[NH]c2ccccc2-c2cccc[c]21.CCC(C)(C)O.CS(C)=O.O>Cc1cc(O)ccc1-c1nc(C(=O)NCc2ccc(F)cc2)c(O)c2ncccc12

Participants

10

Reactant 2

HCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamideHCID 574432723-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 3

HCID 7095BiphenylHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamideHCID 178428974HCID 178428974, compound

Reagents, catalysts & solvents 5

HCID 178454896HCID 178454896, compoundCatalystHCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolventHCID 64052-Methyl-2-butanolSolventHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineOther

Workup

  1. additionAfter 22 hours the crude reactions were diluted with 3 x 1 uL 0.5 M AcOH in DMSO (containing PhPh as an internal standard). The reactions were mixed after each dispense operation.
  2. aliquotMosquito(R) was used to transfer 1 uL of each quenched reaction from the 1,536-well reaction plate to 384-well analytical plates containing 60 uL DMSO for analysis.

Sources & evidence

ORD record
ord-ddc7b22bd36a4e8e9d06875a9dfeb913
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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