4-Bromoanisole → Methyl 2-(4-methoxyanilino)-2-methylpropanoate

HRID 167

Reaction equation

HRID 167 reaction equation
COC(=O)C(C)(C)N.COc1ccc(Br)cc1>CC(=O)O.CC(=O)O.CCC(C)(C)[O-].CCCCP(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2.FC(F)(F)c1ccccc1.[Na+].[Pd]>COC(=O)C(C)(C)Nc1ccc(OC)cc1

Participants

7

Reactant 2

HCID 77304-BromoanisoleHCID 4186341Methyl 2-amino-2-methylpropanoate

Product 1

HCID 60992690Methyl 2-(4-methoxyanilino)-2-methylpropanoateYield 0%

Reagents, catalysts & solvents 4

HCID 2733478Sodium 2-methylbutan-2-olateReagentHCID 4144353Palladium (II) acetateCatalystHCID 11371790Bis(adamantan-1-yl)(butyl)phosphaneCatalystHCID 7368(Trifluoromethyl)benzeneSolvent

Conditions

Temperature
180 °C

Procedure

1-bromo-4-methoxybenzene (0.060 mL, 0.47 mmol), methyl 2-amino-2-methylpropanoate (0.05 g, 0.43 mmol), sodium 2-methylbutan-2-olate (0.052 g, 0.47 mmol), diacetoxypalladium (2.68 mg, 0.01 mmol) and methyl 2-(4-methoxyphenylamino)-2-methylpropanoate (0.00 µg) was added to a microwave vial. (TRIFLUOROMETHYL)-BENZENE (0.5 mL) was used as solvent (1-1.2 mL/mmol amine). The mixture was heated in microwave at 180° for 60min. No conversion of startingmaterial was observed.

Sources & evidence

ORD record
ord-6a2eab081b6a474896fa34b3a81f3801
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

Loading…