Ethanethiol → 3-[3-Cyano-4-[(1-pyrrolidinyl)methyl]benzyl]-6-hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene

HRID 1387089Notes

Reaction equation

HRID 1387089 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[CH2:35][N:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1)[CH2:6][C:7]1[C:8]2[CH:29]=[CH:28][C:27]([O:30]C)=[CH:26][C:9]=2[S:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:14][CH:13]=1)#[N:2].C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[CH2:35][N:36]1[CH2:37][CH2:38][CH2:39][CH2:40]1)[CH2:6][C:7]1[C:8]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][C:9]=2[S:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)=[CH:14][CH:13]=1)#[N:2]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 211829133-[3-Cyano-4-[(1-pyrrolidinyl)methyl]benzyl]-6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene

Product 1

HCID 211828733-[3-Cyano-4-[(1-pyrrolidinyl)methyl]benzyl]-6-hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiopheneYield 68%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

3-[3-Cyano-4-[(1-pyrrolidinyl)methyl]benzyl]-6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene (60 mg, 0.11 mmol) in dichloroethane (4 mL) at 0° C. under argon was treated with ethanethiol (0.1 mL) and aluminum chloride (100 mg) for 3 h before quenching with saturated aqueous sodium bicarbonate solution (10 mL). The stirring was allowed to continue for 1 h at ambient temperature. The resulting mixture was diluted with saturated aqueous sodium bicarbonate solution (50 mL) and extracted with dichloromethane (50 mL×3). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Chromatography with Et3N:MeOH:EtOAc (5:5:90) afforded the title compound as a white foam (40 mg, 68%).

Workup

  1. custombefore quenching with saturated aqueous sodium bicarbonate solution (10 mL)
  2. additionThe resulting mixture was diluted with saturated aqueous sodium bicarbonate solution (50 mL)
  3. extractionextracted with dichloromethane (50 mL×3)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f6296e9cde4487686e354ca70e07784
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

Loading…