Morpholine → Ethyl 3-morpholinobenzoate

HRID 607

Reaction equation

HRID 607 reaction equation
C1COCCN1.CCOC(=O)c1cccc(Br)c1>CC(=O)O.CC(=O)O.Cc1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CCOC(=O)c1cccc(N2CCOCC2)c1

Participants

7

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 3-bromobenzoate (0.070 mL, 0.44 mmol), cesium carbonate (427 mg, 1.31 mmol), diacetoxypalladium (4.90 mg, 0.02 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (5.44 mg, 8.73 µmol) and morpholine (0.042 mL, 0.48 mmol) in toluene (2 mL) was refluxed for 1h. The reaction mixture was cooled and filtered through celite. The celite was washed with EtOAc. The solvent was removed under reduced pressure. The residue was purified by automated flash chromatography on a SNAP 25 g column. A gradient from 0% to 50% of EtOAc in Heptane over 10CV was used as mobile phase. The product was collected using the wavelength 254 nm.

Sources & evidence

ORD record
ord-0fa3456b7ef04add84c9ed9afa8e014e
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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