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

HRID 1335736Notes

Reaction equation

HRID 1335736 reaction equation
Brc1cccnc1.c1ccc(C2CCNCC2)cc1>CC(C)(C)c1ccc(C=[CH](c2ccc(C(C)(C)C)cc2)->[Ni](<-[CH](=Cc2ccc(C(C)(C)C)cc2)c2ccc(C(C)(C)C)cc2)<-[CH](=Cc2ccc(C(C)(C)C)cc2)c2ccc(C(C)(C)C)cc2)cc1.CS(C)=O.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.[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 1.337%

Reagents, catalysts & solvents 4

HCID 23672319Sodium trimethylsilanolateReagentHCID 11767928N,N'-[(1S,2S)-Cyclohexane-1,2-diyl]bis[2-(diphenylphosphanyl)naphthalene-1-carboxamide]CatalystHCID 178440864HCID 178440864, 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-2c4d13b22ca94a009873b9128b92ef90
Source dataset
High-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
Original link
View source

Reaction notes

Loading…