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

HRID 1340644Notes

Reaction equation

HRID 1340644 reaction equation
Brc1cccnc1.c1ccc(C2CCNCC2)cc1>CC(C)(C)[O-].COC(=O)c1ccnc(-c2cc(C(=O)OC)ccn2)c1.CS(C)=O.C[O]1CC[O](C)->[Ni]<-1([Cl])[Cl].[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 20.31%HCID 1398883374-(4-Phenylpiperidin-1-yl)pyridineYield 20.277%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 326419Dimethyl [2,2'-bipyridine]-4,4'-dicarboxylateCatalystHCID 178486304HCID 178486304, 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-6b38019472c94da383e9e0c6863e7d23
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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