5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide → Biphenyl

HRID 609006Notes

Reaction equation

HRID 609006 reaction equation
CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1.CC1(C)OB(c2cn(S(=O)(=O)c3ccccc3)c3ncccc23)OC1(C)C.O=C(NCc1ccc(F)cc1)c1nc(Br)c2cccnc2c1O>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(NCc1ccc(F)cc1)c1nc(-c2cn(S(=O)(=O)c3ccccc3)c3ncccc23)c2cccnc2c1O

Participants

10

Reactant 2

HCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamideHCID 455881371-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine

Product 3

HCID 7095BiphenylHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamideHCID 178523003HCID 178523003, 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-a479ee61ec7c4565ae85d0314a0af7b0
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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