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

HRID 608437Notes

Reaction equation

HRID 608437 reaction equation
Brc1ccc(-c2ccccc2)cn1.CN(C)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1.O=P(O)(O)O.[K]>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>CN(C)c1ccc(-c2ccc(-c3ccccc3)cn2)cc1

Participants

9

Reactant 2

HCID 2758659N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 27628752-Bromo-5-phenylpyridine

Product 3

HCID 7095BiphenylHCID 27628752-Bromo-5-phenylpyridineHCID 178482637HCID 178482637, compound

Reagents, catalysts & solvents 4

HCID 178458464HCID 178458464, compoundCatalystHCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolvent2×HCID 16218557Phosphoric acid (potassium)Other

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-1722a8305ee6492892a60697b9558e12
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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