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

HRID 609075Notes

Reaction equation

HRID 609075 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)(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>O=C(NC1(c2cccc(-c3cc(-c4cc5c([nH]4)CCNC5=O)ccn3)c2)CC1)OCc1ccccc1

Participants

10

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 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-4965c99db539484b9b28037d16293687
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
View source

Reaction notes

Loading…