Sodium Iodide → 3-(5-(cyanomethyl)-3-thienyl)-1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carbonitrile

HRID 2206093Notes

Reaction equation

HRID 2206093 reaction equation
[C:1]([CH2:3][C:4]1[S:8][CH:7]=[C:6]([C:9]2[C:13]3[C:14]([O:20]C)=[N:15][CH:16]=[C:17]([C:18]#[N:19])[C:12]=3[N:11]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:10]=2)[CH:5]=1)#[N:2].[I-].[Na+].Cl[Si](C)(C)C>C(#N)C>[C:1]([CH2:3][C:4]1[S:8][CH:7]=[C:6]([C:9]2[C:13]3[C:14](=[O:20])[NH:15][CH:16]=[C:17]([C:18]#[N:19])[C:12]=3[N:11]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:10]=2)[CH:5]=1)#[N:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 1179882083-(5-(cyanomethyl)-3-thienyl)-1-cyclopentyl-4-methoxy-1H-pyrrolo[3,2-c]pyridine-7-carbonitrile

Product 1

HCID 1179882943-(5-(cyanomethyl)-3-thienyl)-1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carbonitrileYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(5-(cyanomethyl)-3-thienyl)-1-cyclopentyl-4-methoxy-1H-pyrrolo[3,2-c]pyridine-7-carbonitrile (220 mg) in acetonitrile (5 mL) were added sodium iodide (182 mg) and chloro(trimethyl)silane (0.388 mL), and the mixture was stirred at 50° C. for 3 hr. The reaction mixture was allowed to be cooled to room temperature, and filtered, and the obtained solid was washed with acetonitrile and water, and dried under reduced pressure to give the title compound (146 mg).

Workup

  1. temperatureto be cooled to room temperature
  2. filtrationfiltered
  3. washthe obtained solid was washed with acetonitrile and water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-7b3da87a6abc4615b1ffb743e9500340
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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