(4-(Cyclopentylcarbamoyl)phenyl)boronic acid → Biphenyl

HRID 608100Notes

Reaction equation

HRID 608100 reaction equation
CC(=O)NC(C)(C)[C@@H]1CC2(CCN(C(=O)OC(C)(C)C)CC2)c2cc(Cl)c(C)cc21.CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1.O=C(NC1CCCC1)c1ccc(B(O)O)cc1>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>CC(=O)NC(C)(C)[C@@H]1CC2(CCN(C(=O)OC(C)(C)C)CC2)c2cc(-c3ccc(C(=O)NC4CCCC4)cc3)c(C)cc21

Participants

10

Reactant 2

HCID 2773358(4-(Cyclopentylcarbamoyl)phenyl)boronic acidHCID 24805585tert-Butyl (R)-3-(2-acetamidopropan-2-yl)-6-chloro-5-methyl-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

Product 3

HCID 7095BiphenylHCID 24805585tert-Butyl (R)-3-(2-acetamidopropan-2-yl)-6-chloro-5-methyl-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylateHCID 178474758HCID 178474758, compound

Reagents, catalysts & solvents 5

HCID 178454896HCID 178454896, compoundCatalystHCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolventHCID 64052-Methyl-2-butanolSolventHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneOther

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-965627586b8d422292c9234f568a5318
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
View source

Reaction notes

Loading…