Sodium hydride → HCID 71617258, compound

HRID 626191Notes

Reaction equation

HRID 626191 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH2:5][SH:6].[H-].[Na+].Cl[C:10]1[N:15]=[CH:14][C:13](/[C:16](/[C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[C:17](\[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)/[CH2:18][CH3:19])=[CH:12][CH:11]=1>C1COCC1>[CH3:2][NH:3][CH2:4][CH2:5][S:6][C:10]1[N:15]=[CH:14][C:13](/[C:16](/[C:26]2[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=2)=[C:17](\[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)/[CH2:18][CH3:19])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 214693Ethanethiol, 2-(methylamino)-, hydrochlorideHCID 71617026(Z)-4-(1-(6-chloropyridin-3-yl)-2-phenylbut-1-enyl)phenol

Product 1

HCID 71617258HCID 71617258, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(methylamino)ethanethiol hydrochloride (217 mg, 10 eq) in 20 mL anhydrous THF was added NaH (120 mg, 12 eq) at 0° C. After the mixture was stirred at rt for 1 h, (Z)-4-(1-(6-chloropyridin-3-yl)-2-phenylbut-1-enyl)-phenol (80 mg, 1.0 eq, made from example 1) was added. The reaction mixture was heated under reflux for 48 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 (75 mg, 81% yield). 1H NMR (400 MHz, CDCl3) δ 7.89 (dd, J=2.4 Hz, 0.8 Hz, 1H), 7.13-7.21 (m, 3H), 7.05-7.10 (m, 4H), 6.95 (dd, J=8.4 Hz, 2.4 Hz, 1H), 6.83 (d, J=8.4 Hz, 1H), 6.79 (d, J=8.4 Hz, 2H), 3.23 (t, J=6.4 Hz, 2H), 2.84 (t, J=6.4 Hz, 2H), 2.50 (q, J=7.2 Hz, 2H), 2.41 (s, 3H), 0.93 (t, J=7.2 Hz, 3H); m/z=391[M+1]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 48 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-6c747f4f974947938152dea817a422cb
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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