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

Reaction equation

COc1ccc(Br)cc1.Cc1ccc(N)cc1>CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.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>COc1ccc(Nc2ccc(C)cc2)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-03fbfc065769497da698cc287485d097
Source dataset: Ahneman
DOI: 10.1126/science.aar5169

Reaction notes

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Participants

Reactant 2

HCID 77304-Bromoanisole

HCID 7813p-Toluidine

Product 1

HCID 114358284-Methoxy-4'-methyldiphenylamineYield 51.9%

Reagents, catalysts & solvents 3

HCID 33931062,N'3,N'3,N3,N3,N'5,N'5,N5,N5-nonamethyl-2,4,6-triaza-3lambda5,5lambda5-diphosphaocta-3,5-diene-3,3,5,5-tetramineReagent

HCID 178492609HCID 178492609, compoundCatalyst

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-03fbfc065769497da698cc287485d097
Source dataset: Ahneman
DOI: 10.1126/science.aar5169

Reaction notes

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