2-Bromo-6-methoxypyridine → 1-[(Z)-1-(4-chlorophenyl)prop-1-enyl]-1-(4-methoxyphenyl)-3-(6-methoxy-2-pyridinyl)-3-methylurea
Reaction equation
C/C=C(/c1ccc(Cl)cc1)N(C(=O)NC)c1ccc(OC)cc1.COc1cccc(Br)n1>CC(C)(C)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.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.[Na+].[Pd].[Pd]>C/C=C(/c1ccc(Cl)cc1)N(C(=O)N(C)c1cccc(OC)n1)c1ccc(OC)cc1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 110 °C
Procedure
(Z)-1-(1-(4-chlorophenyl)prop-1-enyl)-1-(4-methoxyphenyl)-3-methylurea (0.400 g, 1.21 mmol),2-bromo-6-methoxypyridine (0.292 ml, 2.42 mmol),SODIUM TERT- BUTOXIDE (0.349 g, 3.63 mmol),XANTPHOS (0.070 g, 0.12 mmol) and Pd2(dba)3 (0.055 g, 0.06 mmol) were dissolved intoluene (11.80 ml) and sparged under nitrogen for 1 hour. The resulting mixture was then heated to 110 °C for 48 hours or unitil conversion was complete by TLC. NH4Cl (10 mL) was added and the mixture was extracted twice (EtOAc 20 mL). The organic phases were combined, washed with brine (20 mL), dried (MgSO4) and the solvent removed under reduced pressure. The crude product was then purified by flash column chromatography to give (Z)-1-(1-(4-chlorophenyl)prop-1-enyl)-1-(4-methoxyphenyl)-3-(6-methoxypyridin-2-yl)-3-methylurea (0.381 g, 72.0 %)
Sources & evidence
- ORD record
- ord-055a4c71f284445f89aad15e03c56285
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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