3-Pyridinylboronic acid → Biphenyl

HRID 608974Notes

Reaction equation

HRID 608974 reaction equation
CN(C)C(=NC(C)(C)C)N(C)C.O=C(NCc1ccc(F)cc1)c1nc(Br)c2cccnc2c1O.OB(O)c1cccnc1>CC(C)c1cc(C(C)C)c(-c2ccccc2[PH](C2CCCCC2)(C2CCCCC2)[Pd]2([O]S(C)(=O)=O)[NH]c3ccccc3-c3cccc[c]32)c(C(C)C)c1.CS(C)=O.O>O=C(NCc1ccc(F)cc1)c1nc(-c2cccnc2)c2cccnc2c1O

Participants

9

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

Product 3

HCID 7095BiphenylHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamideHCID 168301685HCID 168301685, compound

Reagents, catalysts & solvents 4

HCID 178439024HCID 178439024, compoundCatalystHCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolvent2×HCID 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-346e491edb4d475ab936e0c5eb656d5e
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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