Tetrahydrofuran → Methyl 2-amino-5-methoxy-3-methylbenzoate
Reaction equation
[NH2:1][C:2]1C(OC)=CC(Br)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CB(O)O.[F-].[K+].[C:21]([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[CH2:34]1[CH2:38][O:37][CH2:36][CH2:35]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:1][C:2]1[C:35]([CH3:21])=[CH:34][C:38]([O:37][CH3:36])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of methyl 2-amino-5-bromo-3-methoxybenzoate (6.50 g, 25 mmol), methylboronic acid (3.0 g, 50 mmol), potassium fluoride (5.8 g, 100 mmol) and tri-t-butylphosphonium tetrafluoroborte (0.87 g, 3.0 mmol) in THF (200 mL) was deoxygenated and then backfilled with argon. Tris(dibenzylideneacetone)dipalladium(0) (1.43 g, 1.5 mmol), was added and the mixture was heated at 70° C. for 17 h under an argon atmosphere. The reaction mixture was concentrated and the residue purified by column chromatography (silica gel, 0% to 5% EtOAc in hexanes) to afford methyl 2-amino-5-methoxy-3-methylbenzoate (3.55 g, 73%) 1H NMR consistent.
Workup
- customwas deoxygenated
- concentrationThe reaction mixture was concentrated
- customthe residue purified by column chromatography (silica gel, 0% to 5% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-35df134f9a174ac298eb7dd43559fd3c
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07863271B2
Reaction notes
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