Water → HCID 117987736, compound

HRID 2206068Notes

Reaction equation

HRID 2206068 reaction equation
[C:1]([C:3]1[CH:8]=[N:7][C:6]([O:9]C)=[C:5]2[N:11]([C:19]3[CH:20]=[C:21]([C:24]([O:26][CH3:27])=[O:25])[S:22][CH:23]=3)[N:12]=[C:13]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[C:4]=12)#[N:2].[I-].[Na+].Cl[Si](C)(C)C.O>C(#N)C>[C:1]([C:3]1[C:4]2[C:13]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[N:12][N:11]([C:19]3[CH:20]=[C:21]([C:24]([O:26][CH3:27])=[O:25])[S:22][CH:23]=3)[C:5]=2[C:6](=[O:9])[NH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 117987938HCID 117987938, compound

Product 1

HCID 117987736HCID 117987736, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4-(4-cyano-3-cyclopentyl-7-methoxy-1H-pyrazolo[3,4-c]pyridin-1-yl)thiophene-2-carboxylate (40 mg) in acetonitrile (5 mL) were added sodium iodide (31.4 mg) and chloro(trimethyl)silane (0.066 mL), and the mixture was stirred at 60° C. for 30 min. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (20 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f12c1a9ea9414d548ea0a05ade0d18cf
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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