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

HRID 609156Notes

Reaction equation

HRID 609156 reaction equation
CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1.CN(C)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1.O=C(Nc1ccccc1N1CCNCC1)c1csc(Br)n1>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>CN(C)c1ccc(-c2nc(C(=O)Nc3ccccc3N3CCNCC3)cs2)cc1

Participants

10

Reactant 2

HCID 2758659N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 91494876HCID 91494876, compound

Product 3

HCID 7095BiphenylHCID 25095481HCID 25095481, compoundHCID 91494876HCID 91494876, 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-7ae7bbe439ea4455a76d429440cb2eb0
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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