4-t-Butylbenzenesulfonyl chloride → Methyl 3-(4-tert-butylphenylsulfonamido)thieno[2,3-b]pyridine-2-carboxylate

HRID 1925727Notes

Reaction equation

HRID 1925727 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[C:11]([O:13][CH2:14]C)=[O:12].[C:16]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>N1C=CC=CC=1.O>[C:16]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:1][C:2]2[C:10]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[S:4][C:3]=2[C:11]([O:13][CH3:14])=[O:12])(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 2

HCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 738459Ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate

Product 1

HCID 59180440Methyl 3-(4-tert-butylphenylsulfonamido)thieno[2,3-b]pyridine-2-carboxylateYield 12.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate (0.3 g; 1.35 mmol) in pyridine (10 mL) was added 4-tert-butylbenzenesulfonyl chloride (0.48 g; 2.03 mol). The reaction was stirred at room temperature for 18 hours and then diluted with water and extracted with ethyl acetate. The organic layer was separated and successively washed with aqueous hydrochloric acid (2N) and aqueous saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated under reduced pressure. The crude residue was purified by silica gel chromatography eluting with hexanes/ethyl acetate to yield the title compound as a white solid (0.070 g).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washsuccessively washed with aqueous hydrochloric acid (2N) and aqueous saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified by silica gel chromatography
  8. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-a4869878b4d840e09171b5f06e6b4f2c
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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