Methyl Acrylate → Methyl 3-(5-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)isoindolin-2-yl)propanoate

HRID 1172979Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[CH2:22][NH:21][CH2:20]4)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[C:26]([O:30][CH3:31])(=[O:29])[CH:27]=[CH2:28]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[CH2:22][N:21]([CH2:28][CH2:27][C:26]([O:30][CH3:31])=[O:29])[CH2:20]4)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 90 °C

Procedure

3-(3-chloro-4-isopropoxyphenyl)-5-(isoindolin-5-yl)-1,2,4-oxadiazole (16.7 mg, 0.047 mmol) was added to a 2 mL microwave vial equipped with a stirring bar. Methyl acrylate (8.45 μL, 0.094 mmol), and methanol (1.0 mL) were added, the vial capped, and the reaction heated to 90° C. for 20 min under microwave irradiation (300 W). After 20 minutes, another aliquot of methyl acrylate (8.45 μL, 0.094 mmol) was added, the vial was re-sealed, and heated to 110° C. for 40 min under microwave irradiation (300 W). Reaction was then concentrated and dried under vacuum overnight to give crude methyl 3-(5-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)isoindolin-2-yl)propanoate as a yellow oil (21.6 mg, 104%). The product was used without further purification. LCMS (Table 1, Method c) Rt=2.85 min, m/z 442.45 (M+H)+

Workup

customvial equipped with a stirring bar
customthe vial was re-sealed
temperatureheated to 110° C. for 40 min under microwave irradiation (300 W)
customReaction
concentrationwas then concentrated
customdried under vacuum overnight

Sources & evidence

ORD record: ord-22c710985a0844488372d8246ac8466f
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834039B2

Reaction notes

Loading…