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

HRID 608553Notes

Reaction equation

HRID 608553 reaction equation
CN(C)C(=NC(C)(C)C)N(C)C.CN(C)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1.COC(=O)[C@@H]1C[C@@H](OC(=O)N2Cc3cccc(Br)c3C2)CN1C(=O)OCc1ccccc1>CCC(C)(C)O.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>COC(=O)[C@@H]1C[C@@H](OC(=O)N2Cc3cccc(-c4ccc(N(C)C)cc4)c3C2)CN1C(=O)OCc1ccccc1

Participants

10

Reactant 2

HCID 2758659N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 547543691-Benzyl 2-methyl (2S,4R)-4-((4-bromoisoindoline-2-carbonyl)oxy)pyrrolidine-1,2-dicarboxylate

Product 3

HCID 7095BiphenylHCID 547543691-Benzyl 2-methyl (2S,4R)-4-((4-bromoisoindoline-2-carbonyl)oxy)pyrrolidine-1,2-dicarboxylateHCID 178501338HCID 178501338, compound

Reagents, catalysts & solvents 5

HCID 178482905HCID 178482905, 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-57d16fba6fcd43dcba0742c005f8d223
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
View source

Reaction notes

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