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4-Fluoro-N-methylaniline → methyl 2-(4-fluoro-N-methylanilino)pyridine-4-carboxylate

HRID 584
Notes
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Reaction equation

HRID 584 reaction equation
CNc1ccc(F)cc1.COC(=O)c1ccnc(Br)c1>Cc1ccccc1.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].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>COC(=O)c1ccnc(N(C)c2ccc(F)cc2)c1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 680244-Fluoro-N-methylanilineHCID 38477682-Bromo-isonicotinic acid methyl ester

Product 1

HCID 108379206methyl 2-(4-fluoro-N-methylanilino)pyridine-4-carboxylateYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 27342162-(Dicyclohexylphosphino)biphenylCatalyst
On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

In a 100 mL round-bottomed flask (t=g) was methyl 2-bromoisonicotinate (.5 g, 2.31 mmol), 4-fluoro-N-methylaniline (0.348 g, 2.78 mmol), and CS2CO3 (1.056 g, 3.24 mmol) in toluene (16 mL) to give a yellow suspension. Pd2dba3 (0.106 g, 0.12 mmol) and biphenyl-2-yldicyclohexylphosphine (0.122 g, 0.35 mmol) were added. Reaction was allowed to stir overnight. LC/MS in the morning revealed little product had formed. Something with mass 272 dominated. Reaction was discarded.

Sources & evidence

ORD record
ord-3a62166a30464afb9cbe502b267cbcba
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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