5-(2-Pyridyl)thiophene-2-sulfonyl chloride → HCID 69314632, compound

HRID 1394046Notes

Reaction equation

HRID 1394046 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][NH2:15])[CH2:8][CH2:7]1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[S:30][C:29]([S:31](Cl)(=[O:33])=[O:32])=[CH:28][CH:27]=1>N1C=CC=CC=1.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][CH2:14][NH:15][S:31]([C:29]2[S:30][C:26]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=3)=[CH:27][CH:28]=2)(=[O:32])=[O:33])[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 27372315-(2-Pyridyl)thiophene-2-sulfonyl chlorideHCID 69314656HCID 69314656, compound

Product 1

HCID 69314632HCID 69314632, compoundYield 21.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

The product of Example 3, Step (d) (0.3 g) was dissolved in pyridine (1 ml) and CH2Cl2 (4 ml). 5-Pyridin-2-yl-thiophene-2-sulfonyl chloride (0.317 g) [dissolved in CH2Cl2 (4 ml)] was then added and the reaction left to stir for 1 hr. The reaction mixture was poured onto flash silica and the silica flushed with 5% MeOH/94% CH2Cl2/1% aq NH3 as eluent. Evaporation of solvent and purification using reverse phase HPLC {with a gradient eluent system [25% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%)]} gave the title compound as a solid (0.120 g).

Workup

  1. waitthe reaction left
  2. additionThe reaction mixture was poured onto flash silica
  3. customthe silica flushed with 5% MeOH/94% CH2Cl2/1% aq NH3 as eluent
  4. customEvaporation of solvent and purification

Sources & evidence

ORD record
ord-1382b9ba38dc49cd80146bfb44989ec5
Source dataset
uspto-grants-2008_03
Patent number
US07348341B2

Reaction notes

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