4-Toluenesulfonyl chloride → HCID 90388503, compound

HRID 2205236Notes

Reaction equation

HRID 2205236 reaction equation
[S:1]1[C:9]2[C:8](=[O:10])[CH2:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>C1COCC1>[CH3:20][C:19]1[CH:21]=[CH:22][C:16]([S:13]([O:10][C:8]2[C:9]3[S:1][CH:2]=[CH:3][C:4]=3[CH:5]=[N:6][CH:7]=2)(=[O:15])=[O:14])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 21997827HCID 21997827, compound

Product 1

HCID 90388503HCID 90388503, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of thieno[3,2-c]pyridin-7(6H)-one (110 mg, 0.728 mmol, 1.0 equiv) in THF (5.00 mL) was added NaH (35 mg, 0.873 mmol, 1.2 equiv) followed by TsCl (180 mg, 0.946 mmol, 1.3 equiv). The reaction mixture was stirred at rt for 2 h, then quenched with water and extracted with ethyl acetate. Purification by column chromatography using 20% ethyl acetate in hexanes elution gave 180 mg of a white solid, 81%.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. customPurification by column chromatography
  4. wash20% ethyl acetate in hexanes elution

Sources & evidence

ORD record
ord-4df3ea75a75f42169c40d8cca1e386d4
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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