p-Toluidine → 4-Methoxy-4'-methyldiphenylamine

HRID 738355Notes

Reaction equation

HRID 738355 reaction equation
COc1ccc(I)cc1.Cc1ccc(N)cc1>CN(C)C(=NC(C)(C)C)N(C)C.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.c1ccc(-c2ccon2)cc1>COc1ccc(Nc2ccc(C)cc2)cc1

Participants

7

Reactant 2

HCID 7813p-ToluidineHCID 696764-Iodoanisole

Product 1

HCID 114358284-Methoxy-4'-methyldiphenylamineYield 45.501%

Reagents, catalysts & solvents 4

HCID 136798Isoxazole, 3-phenyl-ReagentHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineReagentHCID 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-64cc77a09c6046c6a06a4367af3adf50
Source dataset
Ahneman

Reaction notes

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