Iodoethane → HCID 23401175, compound

HRID 1063232Notes

Reaction equation

HRID 1063232 reaction equation
[H-].[Na+].[OH:3][CH2:4][C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([C:12]1[S:20][C:19]2[C:14](=[N:15][CH:16]=[CH:17][C:18]=2[Cl:21])[CH:13]=1)=[O:11].[CH2:22](I)[CH3:23]>CN(C=O)C>[Cl:21][C:18]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:13]=[C:12]([C:10]([N:6]3[CH2:7][CH2:8][CH2:9][C@@H:5]3[CH2:4][O:3][CH2:22][CH3:23])=[O:11])[S:20][C:19]=12

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 20745991HCID 20745991, compound

Product 1

HCID 23401175HCID 23401175, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (80 mg, 2 mmol) was added to a solution of (2R)-(2-hydroxymethyl-pyrrolidin-1-yl)-[7-chloro-thieno[3,2-b]pyridin-2-yl]-methanone (297 mg, 1 mmol) in DMF (5 mL), at 0° C. The reaction mixture was allowed to stir for 20 min, and EtI (234 mg, 1.5 mmol) was added dropwise. After 3 h the reaction was quenched with saturated aqueous KCN (10 mL). The aqueous layer was extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried (Na2SO4), and the solvent was removed. Purification by flash chromatography on silica gel (CH2Cl2/MeOH 94:6) afforded the title compound as a white solid (145 mg, 50%). MS: 326 (MH+); HPLC Rf: 5.11 min; HPLC purity: 97%.

Workup

  1. customAfter 3 h the reaction was quenched with saturated aqueous KCN (10 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×15 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. customthe solvent was removed
  5. customPurification by flash chromatography on silica gel (CH2Cl2/MeOH 94:6)

Sources & evidence

ORD record
ord-2ad9de6533b24f9b93addff3690a060d
Source dataset
uspto-grants-2005_11
Patent number
US06964961B2

Reaction notes

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