Morpholine → 4-(4-Trifluoromethylphenyl)morpholine

HRID 1301958Notes

Reaction equation

HRID 1301958 reaction equation
C1COCCN1.FC(F)(F)c1ccc(Br)cc1>CC1=CC(C)=[O]->[Pd]2([O]1)[O]C(C)=CC(C)=[O]->2.COCCOCCOC.C[Si](C)(C)[O-].O=C(N[C@H]1CCCC[C@@H]1NC(=O)c1c(P(c2ccccc2)c2ccccc2)ccc2ccccc12)c1c(P(c2ccccc2)c2ccccc2)ccc2ccccc12.[Li+]>FC(F)(F)c1ccc(N2CCOCC2)cc1

Participants

9

Reactant 2

HCID 8083MorpholineHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-

Product 3

HCID 2519CaffeineHCID 109333104-(4-Trifluoromethylphenyl)morpholineYield 0%HCID 154202994-(3-(Trifluoromethyl)phenyl)morpholineYield 0%

Reagents, catalysts & solvents 4

HCID 74821Lithium trimethylsilanolateReagentHCID 11767928N,N'-[(1S,2S)-Cyclohexane-1,2-diyl]bis[2-(diphenylphosphanyl)naphthalene-1-carboxamide]CatalystHCID 178427257HCID 178427257, compoundCatalystHCID 8150DiglymeSolvent5×

Conditions

Temperature
60 °C

Workup

  1. customThe foil sealing tape was removed from the plate.
  2. addition3 μL of a 0.0667 M solution of caffeine in DMSO was added to each reaction well using an SPT Labtech Mosquito® liquid handling robot
  3. filtrationThe plates were then centrifuged for 15 to 20 seconds. · Keep liquid
  4. aliquotFollowing centrifugation, 500 nL of the resultant mixture from each well was carefully dispensed into four 384-well analytical plates (Analytical Sales # 38435) using an SPT Labtech Mosquito® liquid handling robot. Each well of these analytical plates contained 30 μL of DMSO with 0.1% acetic acid, pre-dosed by OpenTrons, to facilitate analysis.

Sources & evidence

ORD record
ord-6a58c17ee24b48348dee4de7c3e869ed
Source dataset
High-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
Original link
View source

Reaction notes

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