3,4-Diethoxybenzamide → 2-(3,4-Diethoxyphenyl)-4-(pyridin-4-yl)oxazole

HRID 41124

Reaction equation

Br.Br[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=O.[CH2:12]([O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH3:26])[C:18]([NH2:20])=[O:19])[CH3:13].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:12]([O:14][C:15]1[CH:16]=[C:17]([C:18]2[O:19][CH:3]=[C:4]([C:6]3[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=3)[N:20]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH3:26])[CH3:13]

Participants

Conditions

Temperature: 170 °C

Procedure

In a microwave vial were dissolved 2-bromo-1-(pyridin-4-yl)ethanone hydrobromide (134 mg, 0.478 mmol) and 3,4-diethoxybenzamide (100 mg, 0.478 mmol) in DMF (5 ml) and the reaction was heated at 170° C. for 40 min. The reaction mixture was poured in a saturated solution of NaHCO3 and extracted with EtOAc (50 ml×3). The combined organic phases were washed with a saturated solution of NaCl (2×30 ml) and concentrated under reduced pressure. The product was purified by column chromatography using CH2Cl2:MeOH (95:5) to yield 4 mg (2.7%) of the product. MS (EI) m/z: 311 (M+).

Workup

extractionextracted with EtOAc (50 ml×3)
washThe combined organic phases were washed with a saturated solution of NaCl (2×30 ml)
concentrationconcentrated under reduced pressure
customThe product was purified by column chromatography

Sources & evidence

ORD record: ord-0535fb29f7d64ec2b5bb1177c386bf20
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530503B2

Linked notes

Loading…