3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → Biphenyl

HRID 608812Notes

Reaction equation

HRID 608812 reaction equation
CN(C)C(=NC(C)(C)C)N(C)C.CN1C(=O)C[C@@](C)(c2cc(Br)cs2)N/C1=N/C(=O)OC(C)(C)C.Cc1cc(O)ccc1B1OC(C)(C)C(C)(C)O1>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>Cc1cc(O)ccc1-c1csc([C@]2(C)CC(=O)N(C)/C(=N\C(=O)OC(C)(C)C)N2)c1

Participants

9

Reactant 2

HCID 574432723-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 178481496HCID 178481496, compound

Product 3

HCID 7095BiphenylHCID 178428972HCID 178428972, compoundHCID 178481496HCID 178481496, 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-b1f863fccacd4450b1ab373585bbc57f
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
View source

Reaction notes

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