3-Bromoquinoline → HCID 178519901, compound

HRID 918715Notes

Reaction equation

HRID 918715 reaction equation
Brc1cnc2ccccc2c1.OCc1cocn1>Cl[Pd]Cl.C(CCP(c1ccccc1)c2ccccc2)CP(c3ccccc3)c4ccccc4.C(=O)([O-])[O-].[Cs+].[Cs+].C1COCCO1.[Cu]Br.CSC>OCc1coc(-c2cnc3ccccc3c2)n1.OCc1ncoc1-c1cnc2ccccc2c1.OCc1nc(-c2cnc3ccccc3c2)oc1-c1cnc2ccccc2c1

Participants

9

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-f9afaaa12c794ee191265e09326b06da
Source dataset
C-H activation of oxazoles from the second demo case in the PyParser paper

Reaction notes

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