3-Bromopyridine → 4-(4-Phenylpiperidin-1-yl)pyridine

HRID 1334728Notes

Reaction equation

HRID 1334728 reaction equation
Brc1cccnc1.c1ccc(C2CCNCC2)cc1>COc1ccc(OC)c(P(c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.CS(C)=O.C[Si](C)(C)[O-].O=C1[CH](=Cc2ccccc2)->[Pd]2<-[CH](=Cc3ccccc3)C(=O)[CH](=Cc3ccccc3)->[Pd](<-[CH]1=Cc1ccccc1)<-[CH](=Cc1ccccc1)C(=O)[CH]->2=Cc1ccccc1.[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 1.871%

Reagents, catalysts & solvents 4

HCID 23672319Sodium trimethylsilanolateReagentHCID 44597232Bis(3,5-bis(trifluoromethyl)phenyl)(3,6-dimethoxy-2',4',6'-tri(propan-2-yl)(1,1'-biphenyl)-2-yl)phosphaneCatalystHCID 178516676HCID 178516676, compoundCatalystHCID 679Dimethyl SulfoxideSolvent5×

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-298987250c8c4414b42016897951b1e8
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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