Reaction equation
CN(C)CCN.COc1cc(I)ccc1Br>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]>COc1cc(NCCN(C)C)ccc1BrParticipants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 80 °C
Procedure
A solution of 1-bromo-4-iodo-2-methoxybenzene (0.63 g, 2.01 mmol) dissolved in toluene (15.73 ml) was treated with N1,N1-dimethylethane-1,2-diamine (0.177 g, 2.01 mmol), SODIUM TERT-BUTOXIDE (0.232 g, 2.42 mmol), XANTPHOS (0.116 g, 0.20 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.046 g, 0.05 mmol) under nitrogen. The resulting mixture was stirred at 80 °C in a sealed tube for 2 hours. The reaction mixture was diluted with water (200 mL), and extracted with ethyl acetate (200 mL). The organic was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution 0-10% methanol in dcm. Pure fractions were evaporated to dryness to afford N1-(4-bromo-3-methoxyphenyl)-N2,N2-dimethylethane-1,2-diamine (0.251 g, 45.6 %) as a brown oil.
Sources & evidence
- ORD record
- ord-a7c71c7b356644fcbb6f6b90814539ca
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Linked notes
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