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N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → Biphenyl

HRID 608909
Notes
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Reaction equation

HRID 608909 reaction equation
CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.CN(C)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1.O=C(NCc1ccc(F)cc1)c1nc(Br)c2cccnc2c1O>CC(C)c1cc(C(C)C)c(-c2ccccc2[PH](C(C)(C)C)(C(C)(C)C)[Pd]2([O]S(C)(=O)=O)[NH]c3ccccc3-c3cccc[c]32)c(C(C)C)c1.CS(C)=O.O>CN(C)c1ccc(-c2nc(C(=O)NCc3ccc(F)cc3)c(O)c3ncccc23)cc1
ParticipantsWorkupSources & evidenceReaction notes

Participants

9

Reactant 2

HCID 2758659N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

Product 3

HCID 7095BiphenylHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamideHCID 178482693HCID 178482693, compound

Reagents, catalysts & solvents 4

HCID 178439025HCID 178439025, compoundCatalystHCID 679Dimethyl SulfoxideSolvent4×HCID 962WaterSolventHCID 33931062,N'3,N'3,N3,N3,N'5,N'5,N5,N5-nonamethyl-2,4,6-triaza-3lambda5,5lambda5-diphosphaocta-3,5-diene-3,3,5,5-tetramineOther

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-91f28d3f09b74b4ea0d72df4b748d371
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
DOI
10.1038/s44160-023-00351-1
Original link
View source

Reaction notes

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On this pageParticipantsWorkupSources & evidenceReaction notes