Pyridinium, 1-amino-, iodide (1:1) → HCID 21956522, compound

HRID 2213101Notes

Reaction equation

HRID 2213101 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[I-].[NH2:23][N+:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][N:24]3[N:23]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 2

HCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 21956511HCID 21956511, compound

Product 1

HCID 21956522HCID 21956522, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl(2E)-3-(3-methoxy-4-pyridin-2-ylphenyl)prop-2-enoate (55 mg, 0.2 mmol) and 1-aminopyridinium iodide (86 mg, 0.4 mmol) in DMF (1 mL) was stirred at rt for 2 days open to the atmosphere. The deep purple reaction mixture was diluted with CH2Cl2 (25 mL) and washed with a saturated solution of sodium thiosulfate (25 mL) and brine (25 mL), then dried (MgSO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 3:2) to afford the desired ethyl 2-(3-methoxy-4-pyridin-2-ylphenyl)pyrazolo[1,5-a]pyridin-3-carboxylate as a white solid.

Workup

  1. washwashed with a saturated solution of sodium thiosulfate (25 mL) and brine (25 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 3:2)

Sources & evidence

ORD record
ord-5649251577844a0d8001551b1ae6c183
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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