Pyridine → HCID 22310908, compound

HRID 967102Notes

Reaction equation

HRID 967102 reaction equation
CS(Cl)(=O)=O.[Cl:6][C:7]1[CH:8]=[C:9]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[C:12]1[C:20](O)=O.[N:27]1C=CC=CC=1>>[Cl:6][C:7]1[CH:8]=[C:9]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[C:12]1[C:20]#[N:27]

Participants

4

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 15290299HCID 15290299, compound

Product 1

HCID 22310908HCID 22310908, compoundYield 27%

Conditions

Temperature
0 °C

Procedure

Methanesulphonyl chloride (1 ml) added to a solution of N-(3,4-dichlorobenzyl)indole-2-carboxylic acid (0.23 g) in pyridine at 0° C., and reaction stirred for 2 hours. Ammonia gas was then bubbled through the reaction mixture for 15 mins and then concentrated in vacuo. The residue was dissolved in fresh pyridine, cooled to 0° C. and methanesulphonyl chloride (1 ml) added dropwise. The reaction was stirred for 16 hours, then concentrated in vacuo and residue partitioned between 1N HCl and dichloromethane. Combined organic extracts were dried (MgSO4) and concentrated and the resulting solid purified by column chromatography using dichloromethane-10% ethyl acetate as eluent to give N-(3,4-dichlorobenzyl)-2-cyanoindole as yellow crystals (58 mg, 27%); NMR δ (CD3SOCD3) 5.82 (s, 2H), 6.95-7.70 (m, 7H), 8.03 (m, 1H); M/z (+) 300 (M+), 161, 159; followed by N-(3,4-dichlorobenzyl)indole-2-carboxamide as yellow crystals (37 mg, 16%); M/z (+) 318 (M+), 274, 161, 159, 71, 57.

Workup

  1. customreaction
  2. customAmmonia gas was then bubbled through the reaction mixture for 15 mins
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in fresh pyridine
  5. additionmethanesulphonyl chloride (1 ml) added dropwise
  6. stirringThe reaction was stirred for 16 hours
  7. concentrationconcentrated in vacuo and residue
  8. custompartitioned between 1N HCl and dichloromethane
  9. dry with materialCombined organic extracts were dried (MgSO4)
  10. concentrationconcentrated
  11. customthe resulting solid purified by column chromatography

Sources & evidence

ORD record
ord-0726b4ae3758419a83666b70ff2b1789
Source dataset
uspto-grants-2005_10
Patent number
US06953809B2

Reaction notes

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