N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → Biphenyl

HRID 608078Notes

Reaction equation

HRID 608078 reaction equation
CC(=O)NC(C)(C)[C@@H]1CC2(CCN(C(=O)OC(C)(C)C)CC2)c2cc(Cl)c(C)cc21.CN(C)C(=NC(C)(C)C)N(C)C.CN(C)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1>CN(C)c1ccc([PH](C(C)(C)C)(C(C)(C)C)[Pd]2([O]S(C)(=O)=O)[NH]c3ccccc3-c3cccc[c]32)cc1.CS(C)=O.O>CC(=O)NC(C)(C)[C@@H]1CC2(CCN(C(=O)OC(C)(C)C)CC2)c2cc(-c3ccc(N(C)C)cc3)c(C)cc21

Participants

9

Reactant 2

HCID 2758659N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 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 178474760HCID 178474760, compound

Reagents, catalysts & solvents 4

HCID 178482905HCID 178482905, compoundCatalystHCID 679Dimethyl SulfoxideSolvent4×HCID 962WaterSolventHCID 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-ce68485cf083483abe8df40504cfcf4f
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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