3-Bromoquinoline → HCID 178519901, compound
Reaction equation
Brc1cnc2ccccc2c1.OCc1cocn1>COC1=CC=C(OC)C(C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C)=C1P([C@]34C[C@H]5C[C@H](C[C@H](C5)C4)C3)[C@@]6(C[C@H](C7)C8)CC7C[C@H]8C6.NC9=CC=CC=C9C%10=CC=CC=C%10[Pd]OS(C)(=O)=O.CC(C)(C)C(=O)[O-].[K+].C1COCCO1.[Cu]Br.CSC>OCc1coc(-c2cnc3ccccc3c2)n1.OCc1ncoc1-c1cnc2ccccc2c1.OCc1nc(-c2cnc3ccccc3c2)oc1-c1cnc2ccccc2c1Participants
9
Reactant 2
Product 3
Reagents, catalysts & solvents 4
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
- temperatureThe reactions were then allowed to cool to room temperature
- 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.
- stirringThe reactions were sealed and shaken to ensure a homogenous mixture.
- aliquot50 uL of each reaction mixture was then aspirated and dispensed to the analysis plate.
- 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-39a2ac2ae18d433999e438039eae41a7
- Source dataset
- C-H activation of oxazoles from the second demo case in the PyParser paper
Reaction notes
Loading…