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

HRID 740607Notes

Reaction equation

HRID 740607 reaction equation
Brc1ccccn1.Cc1ccc(N)cc1>CN(C)C(=NC(C)(C)C)N(C)C.COC(=O)c1cc(-c2ccco2)on1.COc1ccc(OC)c([P](C(C)(C)C)(C(C)(C)C)->[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(Nc2ccccn2)cc1

Participants

7

Reactant 2

HCID 7813p-ToluidineHCID 79732-Bromopyridine

Product 1

HCID 27864192-Pyridinamine, N-(4-methylphenyl)-Yield 62.075%

Reagents, catalysts & solvents 4

HCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineReagentHCID 5214769methyl 5-(2-furyl)isoxazole-3-carboxylateReagentHCID 178492620HCID 178492620, 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-4dffdb3da574436496021a752d0deea0
Source dataset
Ahneman

Reaction notes

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