Acetic Acid → Methyl 3-[(1-methylethyl)amino]-5-(pyridin-4-yl)thiophene-2-carboxylate
Reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14].CO[C:19]([CH3:21])=[CH2:20].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCl>[CH3:20][CH:19]([NH:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=2)[S:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14])[CH3:21]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of methyl 3-amino-5-(pyridin-4-yl)thiophene-2-carboxylate (0.469 g, 2.00 mmol), 2-methoxypropene (0.29 mL, 3.0 mmol) and acetic acid (0.114 mL, 2.00 mmol) in dichloromethane (6 mL) was added sodium triacetoxyborohydride (0.636 g, 3.00 mmol), and the reaction was stirred at room temperature overnight. Then, the reaction mixture was poured into sat. NaHCO3 (70 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (50 mL), dried over magnesium sulfate, filtered, and concentrated, and the residue was purified by flash chromatography (Combiflash, silica gel, hexanes to ethyl acetate) to give the title compound (0.256 g, 46%) as a yellow solid:
Workup
- extractionextracted with ethyl acetate (2×50 mL)
- washThe combined organic layers were washed with brine (50 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customthe residue was purified by flash chromatography (Combiflash, silica gel, hexanes to ethyl acetate)
Sources & evidence
- ORD record
- ord-2525a4f7f4244a4ab432b7f44f8b08fa
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691828B2
Reaction notes
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