Potassium Carbonate → HCID 69209072, compound

HRID 2221164Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][N:13]([C:20]2[O:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[CH:21]=2)[C:14](=[O:19])[CH:15]=[CH:16][CH2:17]Br)=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[NH:37]1[CH2:40][CH2:39][CH2:38]1>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][N:13]([C:20]2[O:24][C:23]3[CH:25]=[CH:26][CH:27]=[C:28]([N:37]4[CH2:40][CH2:39][CH2:38]4)[C:22]=3[CH:21]=2)[C:14](=[O:19])[CH:15]=[CH:16][CH3:17])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-[2-(3-benzofuran-2-yl-4-bromobut-2-enoylamino)ethoxy]benzoic acid methyl ester (300 mg, 0.654 mmol)) in dry DMF (4 ml), potassium carbonate (180 mg, 1.31 mmol) and azetidine hydrochloride (41 mg, 0.719 mmol) were added. The reaction mixture was stirred for 4 h at 50° C. The reaction mixture was diluted with ethyl acetate and the resulting suspension was washed with water and brine. After drying the organic phase over sodium sulfate, the solvent was removed under vacuum and the residue was purified by flash chromatography, using mixture of DCM/MeOH (9.5/0.5) as eluent to give 4-[2-(4-azetidin-1-yl-3-benzofuran-2-yl-but-2-enoylamino)ethoxy]benzoic acid methyl ester.

Workup

washthe resulting suspension was washed with water and brine
dry with materialAfter drying the organic phase over sodium sulfate
customthe solvent was removed under vacuum
customthe residue was purified by flash chromatography
additionmixture of DCM/MeOH (9.5/0.5) as eluent

Sources & evidence

ORD record: ord-87479d105ce6477ca442156f9393ae7b
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368476B2

Reaction notes

Loading…