Pyridine → HCID 11334762, compound

HRID 2303466Notes

Reaction equation

HRID 2303466 reaction equation
[Cl:1][C:2]1[C:3]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([NH2:9])=O.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.N1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[C:3]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:15])=[O:16])=[CH:10][C:4]=2[S:5][C:6]=1[C:7]#[N:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 11162076HCID 11162076, compound

Product 1

HCID 11334762HCID 11334762, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirring 0° C. slurry of 3-chloro-6-methanesulfonyl-benzo[b]thiophene-2-carboxylic acid amide 7 (2.8 g, 9.7 mmol) in CH2Cl2 (50 mL) was treated by sequential addition of TFAA (4.0 mL, 5.9 g, 28 mmol) then pyridine (4.0 mL, 3.9 g, 49 mmol). After 2 h, the resulting solution was washed with 0.1 M HCl, dried (Na2SO4), filtered, and evaporated. Chromatography gave 2.1 g (81%) of 3-chloro-6-methanesulfonyl-benzo[b]thiophene-2-carbonitrile 8; 1H NMR δ 3.15 (s, 3H), 8.09 (dd, 1H, J=1.5, 8.6), 8.15 (dd, 1H, J=0.7, 8.6), 8.52 (dd, 1H, J=0.7, 1.5).

Workup

  1. washthe resulting solution was washed with 0.1 M HCl
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-6551bbfe1a5a405bb8d1c7cb8f8b1ec3
Source dataset
uspto-grants-2002_08
Patent number
US06433005B1

Reaction notes

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