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

HRID 1337053Notes

Reaction equation

HRID 1337053 reaction equation
Brc1cccnc1.c1ccc(C2CCNCC2)cc1>CC#[N]->[Cu+](<-[N]#CC)(<-[N]#CC)<-[N]#CC.CN1CCCN2CCCN=C12.CS(C)=O.FC(F)(F)c1ccc(P(c2ccc(C(F)(F)F)cc2)c2ccc(C(F)(F)F)cc2)cc1.O=S(=O)([O-])C(F)(F)F>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 1235837-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-eneReagentHCID 139448Tris(4-trifluoromethylphenyl)phosphineCatalystHCID 178465520HCID 178465520, compoundCatalystHCID 679Dimethyl SulfoxideSolvent5×

Conditions

Temperature
30 °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-90e535946e154e419a880578a94179e6
Source dataset
High-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
Original link
View source

Reaction notes

Loading…