Aniline → Methyl 3-anilino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

HRID 502

Reaction equation

HRID 502 reaction equation
COC(=O)c1cc(Cl)cc(B2OC(C)(C)C(C)(C)O2)c1.Nc1ccccc1>CC(C)(C)P(C(C)(C)C)C(C)(C)C.COCCOC.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=P([O-])([O-])[O-].[K+].[K+].[K+].[Pd].[Pd]>COC(=O)c1cc(Nc2ccccc2)cc(B2OC(C)(C)C(C)(C)O2)c1

Participants

7

Reactant 2

HCID 6115AnilineHCID 56973098Methyl 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Product 1

HCID 11688932Methyl 3-anilino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateYield 0%

Reagents, catalysts & solvents 4

HCID 62657Potassium Phosphate, TribasicReagentHCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

aniline (0.360 mL, 3.95 mmol) was added to methyl 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (900 mg, 3.03 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (139 mg, 0.15 mmol), [Reactants] and potassium phosphate (1546 mg, 7.28 mmol) in degassed DME (10 mL) at 20°C under nitrogen. The reaction was stirred at 100 °C for 24 hours. The reaction mixture was allowed to cool then filtered through celite, washing with ethyl acetate. The filtrate was evaporated under reduced pressure to give a brown residue. Not progressed any further.

Sources & evidence

ORD record
ord-7f4bd58c1e854ed5b839b01e20dd39d2
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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