3-Iodo-7-azaindole → Biphenyl

HRID 609493Notes

Reaction equation

HRID 609493 reaction equation
CC1(C)OB(c2cn(S(=O)(=O)c3ccccc3)c3ncccc23)OC1(C)C.Ic1c[nH]c2ncccc12.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=S(=O)(c1ccccc1)n1cc(-c2c[nH]c3ncccc23)c2cccnc21

Participants

9

Reactant 2

HCID 53770783-Iodo-7-azaindoleHCID 455881371-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine

Product 3

HCID 7095BiphenylHCID 53770783-Iodo-7-azaindoleHCID 178527315HCID 178527315, 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-74ef95e275944acab1b5281e6c82d238
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
View source

Reaction notes

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