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

HRID 608656Notes

Reaction equation

HRID 608656 reaction equation
CC1(C)OB(c2cn(S(=O)(=O)c3ccccc3)c3ncccc23)OC1(C)C.CN(C)C(=NC(C)(C)C)N(C)C.COC(=O)[C@@H]1C[C@@H](OC(=O)N2Cc3cccc(Br)c3C2)CN1C(=O)OCc1ccccc1>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>COC(=O)[C@@H]1C[C@@H](OC(=O)N2Cc3cccc(-c4cn(S(=O)(=O)c5ccccc5)c5ncccc45)c3C2)CN1C(=O)OCc1ccccc1

Participants

9

Reactant 2

HCID 455881371-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridineHCID 547543691-Benzyl 2-methyl (2S,4R)-4-((4-bromoisoindoline-2-carbonyl)oxy)pyrrolidine-1,2-dicarboxylate

Product 3

HCID 7095BiphenylHCID 547543691-Benzyl 2-methyl (2S,4R)-4-((4-bromoisoindoline-2-carbonyl)oxy)pyrrolidine-1,2-dicarboxylateHCID 178501342HCID 178501342, 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-2f846f63334745289921810308c003c0
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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