2-Bromo-4-nitrotoluene → 2-methyl-N-(2-methyl-5-nitrophenyl)quinoline-6-carboxamide

HRID 369

Reaction equation

HRID 369 reaction equation
Cc1ccc([N+](=O)[O-])cc1Br.Cc1ccc2cc(C(N)=O)ccc2n1>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>Cc1ccc2cc(C(=O)Nc3cc([N+](=O)[O-])ccc3C)ccc2n1

Participants

7

Reactant 2

HCID 821892-Bromo-4-nitrotolueneHCID 825739622-Methylquinoline-6-carboxamide

Product 1

HCID 1225895722-methyl-N-(2-methyl-5-nitrophenyl)quinoline-6-carboxamideYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (9.10 mg, 9.94 µmol) was added to 2-bromo-1-methyl-4-nitrobenzene (42.9 mg, 0.20 mmol), 2-methylquinoline-6-carboxamide (37.0 mg, 0.20 mmol), cesium carbonate (194 mg, 0.60 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (11.50 mg, 0.02 mmol) in dioxane (2 mL) at 20°C under nitrogen. The resulting solution was stirred at 100 °C for 6 hours. Reaction seen to be progressing but very sluggish (5% conversion). Reaction abandoned.

Sources & evidence

ORD record
ord-8ca29ea3c13d4e5098dc08cfe112f4d1
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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