4-Methanesulfonylbenzene-1-sulfonyl chloride → Methyl 2-(5-methyl-6-(4-(methylsulfonyl)phenylsulfonyl)-6H-thieno[2,3-b]pyrrol-4-yl)acetate

HRID 422577Notes

Reaction equation

HRID 422577 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[S:7][CH:8]=[CH:9][C:4]=2[C:3]=1[CH2:10][C:11]([O:13][CH3:14])=[O:12].C(O[K])(C)(C)C.[CH3:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23]>C1COCC1>[CH3:1][C:2]1[N:6]([S:31]([C:28]2[CH:27]=[CH:26][C:25]([S:22]([CH3:21])(=[O:24])=[O:23])=[CH:30][CH:29]=2)(=[O:33])=[O:32])[C:5]2[S:7][CH:8]=[CH:9][C:4]=2[C:3]=1[CH2:10][C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 27351824-Methanesulfonylbenzene-1-sulfonyl chlorideHCID 12468203methyl 2-(5-methyl-6H-thieno[2,3-b]pyrrol-4-yl)acetateHCID 178418922HCID 178418922, compound

Product 1

HCID 44176998Methyl 2-(5-methyl-6-(4-(methylsulfonyl)phenylsulfonyl)-6H-thieno[2,3-b]pyrrol-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(5-methyl-6H-thieno[2,3-b]pyrrol-4-yl)acetate (0.059 g, 0.282 mmol) in THF at about 0° C. was added tBuOK (0.044 g, 0.395 mmol), followed by the 4-(methylsulfonyl)-benzene-1-sulfonyl chloride (0.086 g, 0.338 mmol). The reaction mixture was stirred at ambient temperature for about 1 h to give the crude title compound, which was used without further purification. LC/MS (Table 1, Method b) Rt=2.25 min; MS m/z 428 (M+H)+.

Sources & evidence

ORD record
ord-075d5f863493490495c92f2e324faf02
Source dataset
uspto-grants-2012_01
Patent number
US08101645B2

Reaction notes

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