Benzyl (1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)carbamate → Biphenyl

HRID 609070Notes

Reaction equation

HRID 609070 reaction equation
CC1(C)OB(c2cccc(C3(NC(=O)OCc4ccccc4)CC3)c2)OC1(C)C.CN(C)C(=NC(C)(C)C)N(C)C.O=C1NCCc2[nH]c(-c3ccnc(Br)c3)cc21>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>O=C(NC1(c2cccc(-c3cc(-c4cc5c([nH]4)CCNC5=O)ccn3)c2)CC1)OCc1ccccc1

Participants

9

Reactant 2

HCID 129952385Benzyl (1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)carbamateHCID 145711761HCID 145711761, compound

Product 3

HCID 7095BiphenylHCID 145711761HCID 145711761, compoundHCID 178521687HCID 178521687, 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-6530b0d969fb476ca8c4d621c88ecf25
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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