Reaction equation
CN1CCNCC1.COC(=O)c1ccc(OCc2ncccc2Br)cc1>CC(=O)N(C)C.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(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>COC(=O)c1ccc(OCc2ncccc2N2CCN(C)CC2)cc1Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
A mixture of methyl 4-((3-bromopyridin-2-yl)methoxy)benzoate (360 mg, 1.12 mmol), Pd2dba3 (205 mg, 0.22 mmol), BINAP (278 mg, 0.45 mmol), cesium carbonate (728 mg, 2.23 mmol) and 1-methylpiperazine (168 mg, 1.68 mmol) in DMA (10 mL) was stirred at 100 °C for overnight. Sat. NaHCO3 aq was added to the mixture, extracted with ethyl acetate three times, the combined organics were dried over anhydrous Na2SO4, filtered, the filtrate was conc. in vacuo, the residue was purified with ISCO (50% ethyl acetate in hexant to 100% ethyl acetate to 40% mthanol in ethyl acetate) to yield a brown oil as methyl 4-((3-(4-methylpiperazin-1-yl)pyridin-2-yl)methoxy)benzoate (245 mg, 64.2 %).
Sources & evidence
- ORD record
- ord-78ee6abad7ea4585a19ca47439cdac57
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Linked notes
Loading…