4-Bromoanisole → 4-Methoxy-4'-methyldiphenylamine

HRID 737549Notes

Reaction equation

HRID 737549 reaction equation
COc1ccc(Br)cc1.Cc1ccc(N)cc1>CC(C)c1cc(C(C)C)c(-c2ccccc2[P](C(C)(C)C)(C(C)(C)C)->[Pd]2(<-[NH2]c3ccccc3-c3cccc[c]32)[O]S(=O)(=O)C(F)(F)F)c(C(C)C)c1.CCOC(=O)c1cc(C)on1.CN(C)C(=NC(C)(C)C)N(C)C.CS(C)=O>COc1ccc(Nc2ccc(C)cc2)cc1

Participants

7

Reactant 2

HCID 77304-BromoanisoleHCID 7813p-Toluidine

Product 1

HCID 114358284-Methoxy-4'-methyldiphenylamineYield 39.53%

Reagents, catalysts & solvents 4

HCID 76677Ethyl 5-methylisoxazole-3-carboxylateReagentHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineReagentHCID 178439023HCID 178439023, 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-9b6a03b95ebb48e799c71ca2522c5471
Source dataset
Ahneman

Reaction notes

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