Water → 1-{5-[6-(4-Methylpyridin-2-ylamino)pyridin-2-yl]thiophen-2-yl}ethanone
Reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][CH:3]=1.[C:16]([C:19]1[S:23][C:22](B(O)O)=[CH:21][CH:20]=1)(=[O:18])[CH3:17].C(=O)([O-])O.[Na+].O>C(COC)OC.O>[CH3:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:6]2[N:7]=[C:2]([C:22]3[S:23][C:19]([C:16](=[O:18])[CH3:17])=[CH:20][CH:21]=3)[CH:3]=[CH:4][CH:5]=2)[CH:14]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A suspension of (6-bromopyridin-2-yl)-(4-methylpyridin-2-yl)amine (1.00 g, 3.79 mmol), 5-acetylthiophene-2-boronic acid (644 mg, 3.79 mmol), tetrakis triphenylphosphine palladium (440 mg, 0.38 mmol), sodium hydrogen carbonate (480 mg, 5.68 mmol) in dimethoxyethane-water (12 ml) was heated and stirred in an Ar stream at 130° C. for 12 hours. Water was added to the reaction solution and extracted with ethyl acetate. After the organic layer was washed with a saturated brine and dried over anhydrous magnesium sulfate, the residue obtained by concentration in vacuo was washed with tetrahydrofuran-ethyl acetate (1:1), dried, and the title compound (426 mg, 36%) was obtained.
Workup
- temperaturewas heated
- extractionextracted with ethyl acetate
- washAfter the organic layer was washed with a saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe residue obtained by concentration in vacuo
- washwas washed with tetrahydrofuran-ethyl acetate (1:1)
- customdried
Sources & evidence
- ORD record
- ord-281f3d218879450fa3dd0ae2df0ff9c7
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07803801B2
Reaction notes
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