Methylamine → 4-(1-(3-Fluoro-4-(2-(methylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol

HRID 626137Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH3:14])=[CH:7][C:6]=1[F:28].[CH3:29][NH2:30]>CO>[F:28][C:6]1[CH:7]=[C:8]([C:11]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH3:14])[CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH2:2][NH:30][CH3:29]

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred solution of 4-(1-(4-(2-bromoethoxy)-3-fluorophenyl)-2-phenyl but-1-enyl)phenol (111 mg, 0.25 mmol) in 5 mL MeOH was added 1 mL CH3NH2 (30% aq) and the mixture was heated at 85° C. for 18 h. The mixture was extracted with EtOAc. The extract was washed with water and brine, dried over Na2SO4, filtered, concentrated, and purified by column chromatography (CH2Cl2/MeOH (NH3 gas)=10/1) to give the desired product (56 mg, 57% yield, Z/E=1/1) as a beige solid. 1H NMR (400 MHz, CDCl3) δ 7.08-7.11 (m, 5H), 7.03 & 6.77 (d, J=8.6 Hz, 2H), 6.91-6.96 (m, 1H), 6.76 & 6.44 (d, J=8.4 Hz, 2H), 6.51-6.58 (m, 2H), 4.17 & 4.01 (t, J=5.0 Hz, 2H), 3.03 & 2.93 (t, J=5.0 Hz, 2H), 2.55 & 2.48 (s, 3H), 2.47 (q, J=7.6 Hz, 2H), 0.91 (t, J=7.6 Hz, 3H); m/z=392[M+1]+.

Workup

extractionThe mixture was extracted with EtOAc
washThe extract was washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified by column chromatography (CH2Cl2/MeOH (NH3 gas)=10/1)

Sources & evidence

ORD record: ord-b4e029f1ff99416ca50039db6e83195f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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