1-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine → Biphenyl

HRID 608889Notes

Reaction equation

HRID 608889 reaction equation
CC1(C)OB(c2cn(S(=O)(=O)c3ccccc3)c3ncccc23)OC1(C)C.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>CCC(C)(C)O.CN(C)c1ccc([PH](C(C)(C)C)(C(C)(C)C)[Pd]2([O]S(C)(=O)=O)[NH]c3ccccc3-c3cccc[c]32)cc1.CS(C)=O.O>CN1C(=O)C[C@@](C)(c2cc(-c3cn(S(=O)(=O)c4ccccc4)c4ncccc34)cs2)N/C1=N/C(=O)OC(C)(C)C

Participants

10

Reactant 2

HCID 455881371-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridineHCID 178481496HCID 178481496, compound

Product 3

HCID 7095BiphenylHCID 178481496HCID 178481496, compoundHCID 178481507HCID 178481507, compound

Reagents, catalysts & solvents 5

HCID 178482905HCID 178482905, compoundCatalystHCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolventHCID 64052-Methyl-2-butanolSolventHCID 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-d366f78930984f5e8d729f234ff7bea2
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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