4-Bromo-2-nitroanisole → 1-(7-(4-Methoxy-3-nitrophenyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl)ethanone
Reaction equation
CC(=O)N1CC2CNCC(C1)O2.COc1ccc(Br)cc1[N+](=O)[O-]>C1COCCO1.CC(=O)O.CC(=O)O.CC(C)(C)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.[Na+].[Pd]>COc1ccc(N2CC3CN(C(C)=O)CC(C2)O3)cc1[N+](=O)[O-]Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 110 °C
Procedure
1-(9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl)ethanone (36.3 mg, 0.21 mmol), 4-bromo-1-methoxy-2-nitrobenzene (45 mg, 0.19 mmol), diacetoxypalladium (3.48 mg, 0.02 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (8.98 mg, 0.02 mmol) and sodium 2-methylpropan-2-olate (28.0 mg, 0.29 mmol) in dioxane (0.5 mL) were degassed with nitrogen and stirred at 110 °C for 4 hours => _some product formed, by-products are major + degradation_ **_ABANDONED_**
Sources & evidence
- ORD record
- ord-089e5915f1ae4e9e8fd817c5c0f3bd24
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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