Water → methyl 4-(1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylate

HRID 2205991Notes

Reaction equation

HRID 2205991 reaction equation
[CH:1]1([N:6]2[C:14]3[CH:13]=[CH:12][N:11]=[C:10]([O:15]C)[C:9]=3[C:8]([C:17]3[CH:18]=[C:19]([C:22]([O:24][CH3:25])=[O:23])[S:20][CH:21]=3)=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[I-].[Na+].Cl[Si](C)(C)C.O>C(#N)C>[CH:1]1([N:6]2[C:14]3[CH:13]=[CH:12][NH:11][C:10](=[O:15])[C:9]=3[C:8]([C:17]3[CH:18]=[C:19]([C:22]([O:24][CH3:25])=[O:23])[S:20][CH:21]=3)=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 117987631methyl 4-(1-cyclopentyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylate

Product 1

HCID 137010620methyl 4-(1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylateYield 91.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4-(1-cyclopentyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylate (122 mg) in acetonitrile (20 mL) were added sodium iodide (102 mg) and chloro(trimethyl)silane (297 mg), and the mixture was stirred at 60° C. for 20 min. To the reaction mixture was added water, and the mixture was concentrated under reduced pressure to evaporate the acetonitrile. The precipitate in the remaining aqueous solution was collected by filtration to give the title compound (107 mg).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto evaporate the acetonitrile
  3. filtrationThe precipitate in the remaining aqueous solution was collected by filtration

Sources & evidence

ORD record
ord-d8da211fb8a54bc48674384a84b8775b
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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