1,2-Dimethoxyethane → HCID 86613845, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](I)[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[Cl:13].[Br:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[C:17]([F:24])[C:16]=1[O:25][CH3:26].[F-].[Cs+].[CH2:29]([CH2:32]OC)[O:30]C>O>[C:29]([NH:1][C:2]1[CH:7]=[C:6]([C:18]2[CH:19]=[CH:20][C:15]([Br:14])=[C:16]([O:25][CH3:26])[C:17]=2[F:24])[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[Cl:13])(=[O:30])[CH3:32]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
A solution of 4-amino-3-chloro-6-iodopyridine-2-carboxylic acid, methyl ester (1.1 g, 3.0 mmol), 4-bromo-2-fluoro-3-methoxyphenyl boronic acid (1.3 g, 4.5 mmol) and cesium fluoride (0.60 g, 4.0 mmole) in dimethoxyethane (2 mL) and water (2 mL) was de-aerated with a stream of nitrogen for 15 minutes before adding dichlorobis(triphenylphosphine) palladium (0.25 g, 0.4 mmol) and then heated to 85° C. for 2 hours. The reaction mixture was diluted with water (15 mL) and extracted with ethyl acetate (2×15 mL). The combined extracts were washed with brine, dried (sodium sulfate) and concentrated. The residue was purified by chromatography (33% ethyl acetate in hexanes) to give 4-acetylamino-6-(4-bromo-2-fluoro-3-methoxyphenyl)-3-chloropyridine-2-carboxylic acid, methyl ester (1.2 g, 2.8 mmol): mp 164-165° C.
Workup
- extractionextracted with ethyl acetate (2×15 mL)
- washThe combined extracts were washed with brine
- dry with materialdried (sodium sulfate)
- concentrationconcentrated
- customThe residue was purified by chromatography (33% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-ee79c5f4860c4f2f8025c67255b0b577
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07498468B2
Reaction notes
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