4-(5-Bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester → 4-(5-Bromopyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

HRID 723082Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:21][CH3:22])=[C:8]([S:10]([C:13]2[CH:14]=[N:15][C:16](Cl)=[C:17]([Br:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4]>[Zn].C(O)(=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:21][CH3:22])=[C:8]([S:10]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=2)(=[O:11])=[O:12])[CH:9]=1)=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

A flask with 4-(5-bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester (25 mg, 0.06 mmol, Example 118, step c) and zinc dust (4 mg, 0.06 mmol) was dissolved with 1 mL acetic acid and heated to 50° C. for 4 hours. TLC analysis indicated the formation of a new spot. The reaction mixture was concentrated in vacuo and purified by elution through Celite® using 10% MeOH in DCM. The crude product was carried on without further purification. ESI-MS (m/z): Calcd. for C12H10BrNO4S3: 407.9 (M+H); found: 408.1.

Workup

concentrationThe reaction mixture was concentrated in vacuo
custompurified by elution through Celite®
customThe crude product was carried on without further purification

Sources & evidence

ORD record: ord-72fe36e3af8345538a4aece2cce6871d
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138530B2

Reaction notes

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