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Aniline → 2,6-dichloro-N-phenylpyridin-3-amine

HRID 147
Notes
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Reaction equation

HRID 147 reaction equation
Clc1ccc(Br)c(Cl)n1.Nc1ccccc1>C1COCCO1.CC(C)(C)[O-].O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>Clc1ccc(Nc2ccccc2)c(Cl)n1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 6115AnilineHCID 215518193-Bromo-2,6-dichloropyridine

Product 1

HCID 715061202,6-dichloro-N-phenylpyridin-3-amineYield 0%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 634876Binap, (A+-)-Catalyst
HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

BINAP (4.67 mg, 7.50 µmol) and Pd2dba3 (2.289 mg, 2.50 µmol) were dissolved in dioxane (1ml) and flushed with nitrogen. 3-bromo-2,6-dichloropyridine (0.023 g, 0.1 mmol), aniline (0.018 mL, 0.20 mmol) and sodium tert-butoxide (0.014 g, 0.15 mmol) were weight in another flask and flushed with nitrogen. The ligand- Pd mixture was subjoined and the reaction mixture was stirred at 100°C over night. Detection of the reaction was done by LC/MS. LC/MS showed the completion of the reation. the 3-bromo-2,6-dichloropyridine as well as the aniline were gone, but no desired product was detected. NMR verified the observations. The products have not been identified.

Sources & evidence

ORD record
ord-22901a6299a241baa726d8f567bd79ae
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes