Triethylamine → Ethyl (E)-3-(3-aminopyridin-4-yl)acrylate
Reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1Br.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[C:38]([O:42][CH2:43][CH3:44])(=[O:41])[CH:39]=[CH2:40]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1/[CH:40]=[CH:39]/[C:38]([O:42][CH2:43][CH3:44])=[O:41]Participants
Conditions
- Temperature
- 105 °C
Procedure
3-Amino-4-bromopyridine (1.440 ml, 8.32 mmol), palladium (ii) acetate (0.195 g, 0.869 mmol), and tri(o-tolyl)phosphine (0.302 g, 0.992 mmol) were suspended in a mixture of triethylamine (5.0 ml, 35.9 mmol) and acetonitrile (5 mL) in a microwave vial under argon. Ethyl acrylate (1.1 ml, 10.12 mmol) was added and the cap sealed. It was heated in an oil bath to 105° C. After 2 hours the vial was opened and the reaction mixture partitioned between water (100 mL), saturated ammonium chloride (50 mL) and ethyl acetate (200 mL). The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (dichloromethane to ethyl acetate gradient) gave the desired (E)-ethyl 3-(3-aminopyridin-4-yl)acrylate (0.462 g, 2.404 mmol, 28.9% yield).
Workup
- customthe cap sealed
- customthe reaction mixture partitioned between water (100 mL), saturated ammonium chloride (50 mL) and ethyl acetate (200 mL)
- dry with materialThe organic was dried with magnesium sulfate
- customevaporated to dryness under reduced pressure
- customPurification
Sources & evidence
- ORD record
- ord-a067e32143b6451e95f9184c34fd739f
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174992B2
Reaction notes
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