Methylamine → 4-(2-(Benzofuran-5-yl)-1-(4-(2-(methylamino)ethoxy)phenyl)-but-1-enyl)phenol

HRID 626249Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([CH2:29][CH3:30])=[C:11]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20]Cl)=[CH:14][CH:13]=3)=[CH:9][C:4]=2[CH:3]=[CH:2]1.[CH3:31][NH2:32]>CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([CH2:29][CH3:30])=[C:11]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][NH:32][CH3:31])=[CH:14][CH:13]=3)=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred solution of 4-(2-(benzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl) but-1-enyl)phenol (480 mg, 1.0 eq) in 15 mL MeOH was added 5 mL CH3NH2 (aq) and the mixture was heated at 85° C. for 48 h. The organic solvent was removed in vacuo, water was added to the residue and extracted with EtOAc. The extract was dried, concentrated, and purified by column chromatography to give the desired product (230 mg, 49%, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.55 (d, J=2.0 Hz, 1H), 7.36 (s, 1H), 7.27 (d, J=8.8 Hz, 1H), 7.15 (d, J=8.8 Hz, 1H), 7.08 (d, J=8.8 Hz, 1H), 7.01 (d, J=8.8 Hz, 1H), 6.87 (d, J=8.8 Hz, 1H), 6.78 (d, J=8.4 Hz, 1H), 6.74 (d, J=8.8 Hz, 1H), 6.69 (d, J=8.8 Hz, 1H), 6.65 (d, J=2.0 Hz, 1H), 6.47 (d, J=8.8 Hz, 1H), 6.41 (d, J=8.4 Hz, 1H), 4.11 (t, J=4.8 Hz, 1H), 3.92 (t, J=4.8 Hz, 1H), 3.01 (t, J=5.2 Hz, 1H), 2.89 (t, J=5.2 Hz, 1H), 2.45-2.54 (m, 5H), 0.89-0.94 (m, 3H); m/z=414[M+1]+.

Workup

customThe organic solvent was removed in vacuo, water
additionwas added to the residue
extractionextracted with EtOAc
customThe extract was dried
concentrationconcentrated
custompurified by column chromatography

Sources & evidence

ORD record: ord-bf072ddc36c4496e92fb664caece83b1
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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