Cesium carbonate → 2-[4-(Cyanomethoxy)phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene

HRID 1937190Notes

Reaction equation

HRID 1937190 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[C:9]=2[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:39][C:40]#[N:41]>CN(C=O)C.[Cl-].[Na+].O>[C:40]([CH2:39][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[C:9]=2[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)=[CH:20][CH:19]=2)=[CH:4][CH:3]=1)#[N:41]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 224626554-[3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophen-2-yl]phenol

Product 1

HCID 224627722-[4-(Cyanomethoxy)phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A suspension of 2-(4-hydroxyphenyl)-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene (102 mg) and cesium carbonate (386 mg) in DMF (3.0 mL) was treated with bromoacetonitrile (20 μL) while stirring at ambient temperature. Stirring was continued for 2 h and the reaction mixture was diluted with brine (30 mL) and extracted with EtOAc (20 mL×3). The combined organic layers were dried with sodium sulfate and concentrated under reduced pressure. Chromatography with Et3N-EtOAc (0-5%) afforded the product (98 mg).

Workup

  1. stirringStirring
  2. extractionextracted with EtOAc (20 mL×3)
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a277ccfb9d624d8b9101e9d8fe43aa2d
Source dataset
uspto-grants-2002_05
Patent number
US06391901B1

Reaction notes

Loading…