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

HRID 608208Notes

Reaction equation

HRID 608208 reaction equation
CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1.CN1C(=O)C[C@@](C)(c2sccc2Cl)N/C1=N/C(=O)OC(C)(C)C.Cc1cc(O)ccc1B1OC(C)(C)C(C)(C)O1>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>Cc1cc(O)ccc1-c1ccsc1[C@]1(C)CC(=O)N(C)/C(=N\C(=O)OC(C)(C)C)N1

Participants

10

Reactant 2

HCID 574432723-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 178481525HCID 178481525, compound

Product 3

HCID 7095BiphenylHCID 178428970HCID 178428970, compoundHCID 178481525HCID 178481525, 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-522fa89b3e2a47918e440734dd63bf94
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
View source

Reaction notes

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