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

HRID 608968Notes

Reaction equation

HRID 608968 reaction equation
CC1(C)OB(c2ccc(-c3cnccn3)cc2)OC1(C)C.CN(C)C(=NC(C)(C)C)N(C)C.O=C(NCc1ccc(F)cc1)c1nc(Br)c2cccnc2c1O>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=C(NCc1ccc(F)cc1)c1nc(-c2ccc(-c3cnccn3)cc2)c2cccnc2c1O

Participants

9

Reactant 2

HCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamideHCID 583826242-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrazine

Product 3

HCID 7095BiphenylHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamideHCID 178522997HCID 178522997, 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-6ebe1ae983294387b6a6b19a4b23f207
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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