Methylamine → (Z)-2-fluoro-4-(1-(4-hydroxyphenyl)-1-(4-(2-(methylamino)-ethoxy)phenyl)but-1-en-2-yl)phenol

HRID 626141Notes

Reaction equation

HRID 626141 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([F:22])[CH:16]=2)[CH2:13][CH3:14])=[CH:7][CH:6]=1.[CH3:30][NH2:31]>CO>[F:22][C:17]1[CH:16]=[C:15](/[C:12](/[CH2:13][CH3:14])=[C:11](/[C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)\[C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:31][CH3:30])=[CH:6][CH:7]=2)[CH:20]=[CH:19][C:18]=1[OH:21]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 1235113284-(1-(4-(2-Chloroethoxy)phenyl)-1-(4-hydroxyphenyl)but-1-en-2-yl)-2-fluorophenol

Product 1

HCID 71617723(Z)-2-fluoro-4-(1-(4-hydroxyphenyl)-1-(4-(2-(methylamino)-ethoxy)phenyl)but-1-en-2-yl)phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 4-(1-(4-(2-chloroethoxy)phenyl)-1-(4-hydroxyphenyl) but-1-en-2-yl)-2-fluorophenol (310 mg, 0.75 mmol) in 10 mL MeOH was added 2 mL CH3NH2 (30% aq). The reaction mixture was heated at 85° C. for 13 h. and 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 (Z)-product (39 mg, white solid) and (E)-product (14 mg, black brown crystal). m/z=408[M+1]+.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (CH2Cl2/MeOH(NH3 gas)=10/1)
  7. customto give the (Z)-product (39 mg, white solid) and (E)-product (14 mg, black brown crystal)

Sources & evidence

ORD record
ord-a8b8a1454f00418590c18782ba445271
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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