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

HRID 626147Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred solution of 4-(1-(4-(2-chloroethoxy)phenyl)-2-phenylbut-1-enyl)-2-fluorophenol in 5 mL MeOH was added 2 mL CH3NH2 (30% aq) and heated at 85° C. overnight. The mixture was extracted with EtOAc, 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 (59% yield, Z/E=1/1 as a white solid. m/z=392[M+1]+.

Workup

extractionThe mixture was extracted with EtOAc
washwashed 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-093293e1f073476788ee6ea5ff4465e7
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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