p-Toluidine → 3-Pyridinamine, N-(4-methylphenyl)-

HRID 739351Notes

Reaction equation

HRID 739351 reaction equation
Cc1ccc(N)cc1.Ic1cccnc1>CN(C)C(=NC(C)(C)C)N(C)C.COC(=O)c1ccno1.COc1ccc(OC)c([P](C23CC4CC(CC(C4)C2)C3)(C23CC4CC(CC(C4)C2)C3)->[Pd]2(<-[NH2]c3ccccc3-c3cccc[c]32)[O]S(=O)(=O)C(F)(F)F)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.CS(C)=O>Cc1ccc(Nc2cccnc2)cc1

Participants

7

Reactant 2

HCID 7813p-ToluidineHCID 707143-Iodopyridine

Product 1

HCID 6035893-Pyridinamine, N-(4-methylphenyl)-Yield 29.298%

Reagents, catalysts & solvents 4

HCID 2736892Methyl isoxazole-5-carboxylateReagentHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineReagentHCID 178492609HCID 178492609, compoundCatalystHCID 679Dimethyl SulfoxideSolvent5×

Conditions

Temperature
60 °C

Procedure

These solutions were added to a 384- well source plate (80 µL per well). The Mosquito HTS liquid handling robot was used to dose each of these solutions (200 nL each) into a 1536-well plate.

Workup

  1. additionNo procedure recorded

Sources & evidence

ORD record
ord-f991f64ed8334849b73c09c1c8f381f8
Source dataset
Ahneman

Reaction notes

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