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

HRID 609132Notes

Reaction equation

HRID 609132 reaction equation
CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1.CC1(C)OB(c2cn(S(=O)(=O)c3ccccc3)c3ncccc23)OC1(C)C.O=C1NCCc2[nH]c(-c3ccnc(Br)c3)cc21>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>O=C1NCCc2[nH]c(-c3ccnc(-c4cn(S(=O)(=O)c5ccccc5)c5ncccc45)c3)cc21

Participants

10

Reactant 2

HCID 455881371-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridineHCID 145711761HCID 145711761, compound

Product 3

HCID 7095BiphenylHCID 145711761HCID 145711761, compoundHCID 178517699HCID 178517699, 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-7324da433a3a46b7b6f37c3d6212553a
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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