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3-Bromoquinoline → HCID 178519901, compound

HRID 918735
Notes
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Reaction equation

HRID 918735 reaction equation
Brc1cnc2ccccc2c1.OCc1cocn1>Cl[Pd]Cl.Clc1cccnc1.CC(C)c2cccc(C(C)C)c2N3CN(C=C3)c4c(cccc4C(C)C)C(C)C.CC(C)(C)C(=O)[O-].[K+].C1COCCO1.[Cu]Br.CSC>OCc1coc(-c2cnc3ccccc3c2)n1.OCc1ncoc1-c1cnc2ccccc2c1.OCc1nc(-c2cnc3ccccc3c2)oc1-c1cnc2ccccc2c1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 2

HCID 214133-BromoquinolineHCID 159305781,3-Oxazol-4-ylmethanol

Product 3

HCID 178519901HCID 178519901, compoundHCID 178519952HCID 178519952, compoundHCID 178520002HCID 178520002, compound

Reagents, catalysts & solvents 4

HCID 23662159
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes
Potassium Trimethylacetate
Reagent
HCID 2724234Bromo(thiobis(methane))copperCatalyst
HCID 16218181Dichloro-[1,3-bis(diisopropylphenyl)-2-imidazolidinyliden]-(3-chloropyridyl)palladium(II)Catalyst
HCID 312751,4-DioxaneSolvent3×

Conditions

Temperature
100 °C

Procedure

- reaction input `pd_catalyst` was added as a solution (2-methyltetrahydrofuran 1 mmol/L) and then the solvent was removed to leave solid solute before adding other reactants/reagents; - stirrer was added after `pd_catalyst` and before `base`; - reaction inputs were prepared inside a glove box but the reaction itself did not happen in a glove box; - the reaction vial was sealed after adding all reaction inputs

Workup

  1. temperatureThe reactions were then allowed to cool to room temperature
  2. additionEach reaction vial was diluted with 500 uL of a pre-prepared solution consisting of 1 umol dibenzylaniline (labelled as an internal standard for the purposes of PyParse analysis) and 20 umol dimethylsulfoxide in acetonitrile.
  3. stirringThe reactions were sealed and shaken to ensure a homogenous mixture.
  4. aliquot50 uL of each reaction mixture was then aspirated and dispensed to the analysis plate.
  5. additionEach well of the analysis plate was diluted with 150 uL of dimethylsulfoxide, and the analysis plate was sealed with polypropylene film.

Sources & evidence

ORD record
ord-3f725689f519483fa7f0882e508cbe89
Source dataset
C-H activation of oxazoles from the second demo case in the PyParser paper
DOI
10.1039/d3dd00167a

Reaction notes

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