Ethyl 4-(3-bromo-8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate → Biphenyl

HRID 608391Notes

Reaction equation

HRID 608391 reaction equation
CC1(C)OB(c2cnc(-n3cccn3)nc2)OC1(C)C.CCOC(=O)N1CCC(=C2c3ccc(Cl)cc3CCc3cc(Br)cnc32)CC1.CN(C)C(=NC(C)(C)C)N(C)C>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>CCOC(=O)N1CCC(=C2c3ccc(Cl)cc3CCc3cc(-c4cnc(-n5cccn5)nc4)cnc32)CC1

Participants

10

Reactant 2

HCID 10742688Ethyl 4-(3-bromo-8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylateHCID 49758770HCID 49758770, compound

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 178473330HCID 178473330, 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-ed21d12f195640baa71877222198f039
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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