Dichloromethane → (7-Chlorothieno[3,2-b]pyridin-2-yl)(pyrrolidin-1-yl)methanone

HRID 1063132Notes

Reaction equation

HRID 1063132 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O-:13])=O)[S:10][C:3]=12.[Li+].S(Cl)(Cl)=O.C(Cl)Cl.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:13])[S:10][C:3]=12

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 31268PyrrolidineHCID 23677819Lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate

Product 1

HCID 11173165(7-Chlorothieno[3,2-b]pyridin-2-yl)(pyrrolidin-1-yl)methanoneYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of lithium 7-chloro-thieno[3,2-b]pyridine-2-carboxylate (0.50 g, 2.4 mmol), thionyl chloride (3.5 mmol, 1.8 ml), CH2Cl2 (20 ml), and DMF (0.2 ml) was heated to reflux. After 3 h the resulting yellow solution was concentrated under reduced pressure, and the residue was suspended in CH2Cl2 (20 mL). Pyrrolidine (2.35 mmol, 167 mg) was then added dropwise. After 12h the reaction mixture was concentrated onto silica gel (5 mL) and purified by flash chromatography on silica gel eluting with CH2Cl2/MeOH (97/3) to afford the title compound as a white solid (360 mg, 57%). MS: 266.9/268.9 (MH+); HPLC Rf: 4.51 min; HPLC purity: 98%.

Workup

  1. concentrationAfter 3 h the resulting yellow solution was concentrated under reduced pressure
  2. concentrationAfter 12h the reaction mixture was concentrated onto silica gel (5 mL)
  3. custompurified by flash chromatography on silica gel eluting with CH2Cl2/MeOH (97/3)

Sources & evidence

ORD record
ord-ef1171b6d1ee4ff88e02867a0f6f4539
Source dataset
uspto-grants-2005_11
Patent number
US06964961B2

Reaction notes

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