Methyl Acrylate → (E)-Methyl 3-(3-aminopyridin-2-YL)acrylate

Temperature

145 °C

The following reaction was performed in duplicate: A glass microwave reaction vessel was charged with 3-amino-2-bromopyridine (2.00 g, 11.56 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.250 g, 0.353 mmol). DMF (10 mL) was added followed by methyl acrylate (4.00 mL, 44.3 mmol) and triethylamine (4.00 mL, 28.7 mmol). The reaction mixture was sealed under argon and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 145° C. for 40 min. The reaction mixtures were combined and the solvent was removed in vacuo. The residue was dissolved in DCM, evaporated onto silica gel and purified by flash chromatography (ISCO, (120 gram HP)) eluting with 2M NH3 in MeOH:CH2Cl2 (0:1-1:39) to give 2.75 g (69%) of a yellow amorphous solid. ESI-MS 179.0 [M+1].

1. customThe following reaction
2. customA glass microwave reaction vessel
3. customThe reaction mixture was sealed under argon
4. customThe reaction mixtures
5. customthe solvent was removed in vacuo
6. dissolutionThe residue was dissolved in DCM
7. customevaporated onto silica gel
8. custompurified by flash chromatography (ISCO, (120 gram HP))
9. washeluting with 2M NH3 in MeOH:CH2Cl2 (0:1-1:39)

ORD record

ord-a0156781118f47a7a0383180547625da

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174992B2