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

HRID 608344Notes

Reaction equation

HRID 608344 reaction equation
CCOC(=O)N1CCC(=C2c3ccc(Cl)cc3CCc3cc(Br)cnc32)CC1.CN(C)C(=NC(C)(C)C)N(C)C.O=C(NC1CCCC1)c1ccc(B(O)O)cc1>CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1[PH](C1CCCCC1)(C1CCCCC1)[Pd]1([O]S(C)(=O)=O)[NH]c2ccccc2-c2cccc[c]21.CS(C)=O.O>CCOC(=O)N1CCC(=C2c3ccc(Cl)cc3CCc3cc(-c4ccc(C(=O)NC5CCCC5)cc4)cnc32)CC1

Participants

9

Reactant 2

HCID 2773358(4-(Cyclopentylcarbamoyl)phenyl)boronic 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 178473327HCID 178473327, compound

Reagents, catalysts & solvents 4

HCID 178458464HCID 178458464, 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-1607c8b6ca954e4daa5ba29e02977284
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
View source

Reaction notes

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