Sodium Iodide → HCID 58612381, compound

HRID 2218105Notes

Reaction equation

HRID 2218105 reaction equation
Cl[CH2:2][CH2:3][C@H:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[CH:12]=[CH:13][S:14][C:7]=12.[Na+].[I-:22]>CC(C)=O>[I:22][CH2:2][CH2:3][C@H:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[CH:12]=[CH:13][S:14][C:7]=12

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 58612385HCID 58612385, compound

Product 1

HCID 58612381HCID 58612381, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 7-[(1R)-(3-Chloro-1-phenyl-propoxy)]-thieno[3,2-b]pyridine (703 mg, 2.3 mmol) in 15 mL of acetone was added NaI (3.5 g, 23 mmol). The resulting solution was allowed to stir at 55° C. for 18 h before removing the acetone in vacuo. The residue was taken up in CH2Cl2 and water. The layers were separated and the aqueous phase was further extracted 2 times with CH2Cl2. The combined organic phase was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography eluting silica gel with hexane:ethyl acetate [100:0 to 1:1] to yield the title compound (0.79 g, 87%); mass spectrum (ion spray): m/z=395.98 (m+1).

Workup

  1. custombefore removing the acetone in vacuo
  2. customThe layers were separated
  3. extractionthe aqueous phase was further extracted 2 times with CH2Cl2
  4. dry with materialThe combined organic phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting silica gel with hexane

Sources & evidence

ORD record
ord-26a8c5d46df54945bbacc66b6cf50382
Source dataset
uspto-grants-2008_08
Patent number
US07410982B2

Reaction notes

Loading…