3-Pyridinylboronic acid → Biphenyl

HRID 608372Notes

Reaction equation

HRID 608372 reaction equation
CCOC(=O)N1CCC(=C2c3ccc(Cl)cc3CCc3cc(Br)cnc32)CC1.CN(C)C(=NC(C)(C)C)N(C)C.OB(O)c1cccnc1>CC(C)c1cc(C(C)C)c(-c2ccccc2[PH](C(C)(C)C)(C(C)(C)C)[Pd]2([O]S(C)(=O)=O)[NH]c3ccccc3-c3cccc[c]32)c(C(C)C)c1.CS(C)=O.O>CCOC(=O)N1CCC(=C2c3ccc(Cl)cc3CCc3cc(-c4cccnc4)cnc32)CC1

Participants

9

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 10742688Ethyl 4-(3-bromo-8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

Product 3

HCID 7095BiphenylHCID 10742688Ethyl 4-(3-bromo-8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylateHCID 168301680HCID 168301680, compound

Reagents, catalysts & solvents 4

HCID 178439025HCID 178439025, compoundCatalystHCID 679Dimethyl SulfoxideSolvent4×HCID 962WaterSolventHCID 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-e1543c47d18d4ed4b952a965c7835517
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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