5-(2-Pyridyl)thiophene-2-sulfonyl chloride → HCID 69310657, compound

HRID 1394049Notes

Reaction equation

HRID 1394049 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:11][C:10]([S:12](Cl)(=[O:14])=[O:13])=[CH:9][CH:8]=1.[CH2:16]([C@H:23]([NH2:41])[C:24]([N:26]1[CH2:31][CH2:30][CH:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[C:35]([F:40])[CH:34]=2)[CH2:28][CH2:27]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[CH2:16]([C@H:23]([NH:41][S:12]([C:10]1[S:11][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:8][CH:9]=1)(=[O:14])=[O:13])[C:24]([N:26]1[CH2:27][CH2:28][CH:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[C:35]([F:40])[CH:34]=2)[CH2:30][CH2:31]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 27372315-(2-Pyridyl)thiophene-2-sulfonyl chlorideHCID 69309205HCID 69309205, compound

Product 1

HCID 69310657HCID 69310657, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-pyridin-2-yl-thiophene-2-sulfonyl chloride (0.072 g) [in CH2Cl2 (5 ml) and dimethyl amino pyridine (0.034 g)] was added a solution of the product of Example 5, Step (b) (0.100 g) in CH2Cl2 (1 ml). The reaction was left to stir for 12 hrs. The reaction mixture was then pre-absorbed onto flash silica and purified by flash silica column chromatography with 2% MeOH/97.5% CH2Cl2/0.5% aq NH3 as eluent. Further purification using flash silica chromatography with 10% MeCN/2% TEA/88% CH2Cl2 eluent gave the title compound as a solid (0.045 g).

Workup

  1. waitThe reaction was left
  2. customThe reaction mixture was then pre-absorbed onto flash silica
  3. custompurified by flash silica column chromatography with 2% MeOH/97.5% CH2Cl2/0.5% aq NH3 as eluent
  4. customFurther purification

Sources & evidence

ORD record
ord-c3f424763f4b46b49b4fe9a79f848177
Source dataset
uspto-grants-2008_03
Patent number
US07348341B2

Reaction notes

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