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

HRID 608910
Notes
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Reaction equation

HRID 608910 reaction equation
CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1.CN(C)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1.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>CN(C)c1ccc(-c2nc(C(=O)NCc3ccc(F)cc3)c(O)c3ncccc23)cc1
ParticipantsWorkupSources & evidenceReaction notes

Participants

10

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 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-57732dc5bc36427c8fb692417a11abe4
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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