3-Bromopyridine → 3-(4-Phenyl-1-piperidinyl)pyridine

HRID 1341697Notes

Reaction equation

HRID 1341697 reaction equation
Brc1cccnc1.c1ccc(C2CCNCC2)cc1>CC(C)(C)P(C(C)(C)C)[c]12->[Fe+2]3456789(<-[cH]([cH]->3[cH-]->41)[cH]->52)<-[c]1(-c2ccccc2)[c]->6(-c2ccccc2)[c]->7(-c2ccccc2)[c-]->8(-c2ccccc2)[c]->91-c1ccccc1.COCCOCCOC.C[Si](C)(C)[O-].[Cu][I].[Na+]>c1ccc(C2CCN(c3cccnc3)CC2)cc1

Participants

9

Reactant 2

HCID 122863-BromopyridineHCID 698734-Phenylpiperidine

Product 3

HCID 2519CaffeineHCID 1223802233-(4-Phenyl-1-piperidinyl)pyridineYield 0%HCID 1398883374-(4-Phenylpiperidin-1-yl)pyridineYield 0%

Reagents, catalysts & solvents 4

HCID 23672319Sodium trimethylsilanolateReagentHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178454875HCID 178454875, 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-a6d9c7fa0a514a0db5f6a301cbc1acca
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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