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 608332Notes

Reaction equation

HRID 608332 reaction equation
CCOC(=O)N1CCC(=C2c3ccc(Cl)cc3CCc3cc(Br)cnc32)CC1.CN(C)C(=NC(C)(C)C)N(C)C.Cc1cc(O)ccc1B1OC(C)(C)C(C)(C)O1>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(O)cc4C)cnc32)CC1

Participants

9

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 574432723-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

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 178473329HCID 178473329, 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-82e585f2d0234609b1d12ab5cfe467fd
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
View source

Reaction notes

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