2-Bromo-5-phenylpyridine → Biphenyl

HRID 608466Notes

Reaction equation

HRID 608466 reaction equation
Brc1ccc(-c2ccccc2)cn1.CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1.CC1(C)OB(c2cccc(C3(NC(=O)OCc4ccccc4)CC3)c2)OC1(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>O=C(NC1(c2cccc(-c3ccc(-c4ccccc4)cn3)c2)CC1)OCc1ccccc1

Participants

10

Reactant 2

HCID 27628752-Bromo-5-phenylpyridineHCID 129952385Benzyl (1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)carbamate

Product 3

HCID 7095BiphenylHCID 27628752-Bromo-5-phenylpyridineHCID 178521689HCID 178521689, compound

Reagents, catalysts & solvents 5

HCID 178482905HCID 178482905, 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-9579f7df222c42f6bb29bec4eb1de23e
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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