1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → Biphenyl

HRID 609235Notes

Reaction equation

HRID 609235 reaction equation
CC1(C)OB(c2cnn(Cc3ccccc3)c2)OC1(C)C.O=C(Nc1ccccc1N1CCNCC1)c1csc(Br)n1.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>O=C(Nc1ccccc1N1CCNCC1)c1csc(-c2cnn(Cc3ccccc3)c2)n1

Participants

9

Reactant 2

HCID 27347711-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 91494876HCID 91494876, compound

Product 3

HCID 7095BiphenylHCID 91494876HCID 91494876, compoundHCID 178521953HCID 178521953, 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-299f2d694bec4c9cbf883599e32a8774
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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