p-Toluidine → 2-Pyridinamine, N-(4-methylphenyl)-

Reaction equation

Cc1ccc(N)cc1.Clc1ccccn1>CC(C)c1cc(C(C)C)c(-c2ccccc2[P](C2CCCCC2)(C2CCCCC2)->[Pd]2(<-[NH2]c3ccccc3-c3cccc[c]32)[O]S(=O)(=O)C(F)(F)F)c(C(C)C)c1.CN1CCCN2CCCN=C12.CS(C)=O>Cc1ccc(Nc2ccccn2)cc1

Participants

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

additionNo procedure recorded

Sources & evidence

ORD record: ord-c4c679e53a5d4acb93685ba5d7588e7a
Source dataset: Ahneman
DOI: 10.1126/science.aar5169

Reaction notes

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Participants

Reactant 2

HCID 7813p-Toluidine

HCID 79772-Chloropyridine

Product 1

HCID 27864192-Pyridinamine, N-(4-methylphenyl)-Yield 29.587%

Reagents, catalysts & solvents 3

HCID 1235837-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-eneReagent

HCID 178439018HCID 178439018, compoundCatalyst

HCID 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

additionNo procedure recorded

Sources & evidence

ORD record: ord-c4c679e53a5d4acb93685ba5d7588e7a
Source dataset: Ahneman
DOI: 10.1126/science.aar5169

Reaction notes

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