2-(Methylamino)ethanol → (Z)-4-(1-(6-(2-(methylamino)ethoxy)pyridin-3-yl)-2-phenylbut-1-enyl)phenol

HRID 626096Notes

Reaction equation

HRID 626096 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:9]1[N:14]=[CH:13][C:12](/[C:15](/[C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[C:16](\[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)/[CH2:17][CH3:18])=[CH:11][CH:10]=1>C1COCC1>[CH3:1][NH:2][CH2:3][CH2:4][O:5][C:9]1[N:14]=[CH:13][C:12](/[C:15](/[C:25]2[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=2)=[C:16](\[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)/[CH2:17][CH3:18])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 24758Sodium hydrideHCID 71617026(Z)-4-(1-(6-chloropyridin-3-yl)-2-phenylbut-1-enyl)phenol

Product 1

HCID 71617032(Z)-4-(1-(6-(2-(methylamino)ethoxy)pyridin-3-yl)-2-phenylbut-1-enyl)phenolYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(methylamino)ethanol (672 mg, 10 eq) in 20 mL anhydrous THF was added NaH (373 mg, 8.0 eq) at 0° C. The mixture was stirred at rt for 1 h, then to the mixture was added (Z)-4-(1-(6-chloropyridin-3-yl)-2-phenylbut-1-enyl)phenol (300 mg, 1 eq, made from example 1). The reaction was heated at reflux for 16 h, cooled, quenched with sat. NH4Cl, and extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography to give the desired product (200 mg, 60% yield). 1H NMR (400 MHz, CDCl3) δ 7.59 (s, 1H), 7.18-7.20 (m, 2H), 7.08-7.16 (m, 3H), 7.01-7.06 (m, 3H), 6.77 (d, J=8.4 Hz, 1H), 6.28 (d, J=8.4 Hz, 1H), 4.28 (t, J=5.2 Hz, 2H), 2.93 (t, J=5.2 Hz, 2H), 2.46-2.55 (m, 5H), 0.92 (t, J=7.6 Hz, 3H); m/z=375 [M+1]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 16 h
  3. temperaturecooled
  4. customquenched with sat. NH4Cl
  5. extractionextracted with CH2Cl2
  6. customThe extract was dried
  7. concentrationconcentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-f575dfa403134b59ac92a05d15068964
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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