(4-(Cyclopentylcarbamoyl)phenyl)boronic acid → Biphenyl

HRID 608693Notes

Reaction equation

HRID 608693 reaction equation
CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.CCn1c(=O)c2c(nc(N[C@@H]3CCC[C@H]3O)n2Cc2ccc(OC)c(Br)c2)n(CCO)c1=O.O=C(NC1CCCC1)c1ccc(B(O)O)cc1>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>CCn1c(=O)c2c(nc(N[C@@H]3CCC[C@H]3O)n2Cc2ccc(OC)c(-c3ccc(C(=O)NC4CCCC4)cc3)c2)n(CCO)c1=O

Participants

9

Reactant 2

HCID 2773358(4-(Cyclopentylcarbamoyl)phenyl)boronic acidHCID 9871410Dasantafil

Product 3

HCID 7095BiphenylHCID 9871410DasantafilHCID 178462857HCID 178462857, compound

Reagents, catalysts & solvents 4

HCID 178439025HCID 178439025, compoundCatalystHCID 679Dimethyl SulfoxideSolvent4×HCID 962WaterSolventHCID 33931062,N'3,N'3,N3,N3,N'5,N'5,N5,N5-nonamethyl-2,4,6-triaza-3lambda5,5lambda5-diphosphaocta-3,5-diene-3,3,5,5-tetramineOther

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-216f47f4a5d143068ccf14ceacebc465
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
View source

Reaction notes

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