2-Bromo-5-phenylpyridine → Biphenyl

HRID 608542Notes

Reaction equation

HRID 608542 reaction equation
Brc1ccc(-c2ccccc2)cn1.CC1(C)OB(C2=CCCCC2)OC1(C)C.CN(C)C(=NC(C)(C)C)N(C)C>CC(C)c1cc(C(C)C)c(-c2ccccc2[PH](C2CCCCC2)(C2CCCCC2)[Pd]2([O]S(C)(=O)=O)[NH]c3ccccc3-c3cccc[c]32)c(C(C)C)c1.CS(C)=O.O>C1=C(c2ccc(-c3ccccc3)cn2)CCCC1

Participants

9

Reactant 2

HCID 27628752-Bromo-5-phenylpyridineHCID 109326752-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 3

HCID 7095BiphenylHCID 27628752-Bromo-5-phenylpyridineHCID 59180846HCID 59180846, compound

Reagents, catalysts & solvents 4

HCID 178439024HCID 178439024, 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-b869584b2edc4c9b864f002d7ffe4148
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
View source

Reaction notes

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