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

HRID 608800Notes

Reaction equation

HRID 608800 reaction equation
CN(C)C(=NC(C)(C)C)N(C)C.CN(C)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1.CN1C(=O)C[C@@](C)(c2cc(Br)cs2)N/C1=N/C(=O)OC(C)(C)C>CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1[PH](C1CCCCC1)(C1CCCCC1)[Pd]1([O]S(C)(=O)=O)[NH]c2ccccc2-c2cccc[c]21.CS(C)=O.O>CN1C(=O)C[C@@](C)(c2cc(-c3ccc(N(C)C)cc3)cs2)N/C1=N/C(=O)OC(C)(C)C

Participants

9

Reactant 2

HCID 2758659N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 178481496HCID 178481496, compound

Product 3

HCID 7095BiphenylHCID 178481496HCID 178481496, compoundHCID 178481504HCID 178481504, compound

Reagents, catalysts & solvents 4

HCID 178458464HCID 178458464, compoundCatalystHCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolvent2×HCID 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-f17215dd46c0433eac3930cc16fe5aa7
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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