Sodium hydride → HCID 10410352, compound

HRID 1611503Notes

Reaction equation

HRID 1611503 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][CH3:11])=[CH:5][C:3]=1[NH2:4].[H-].[Na+].[Br:14][C:15]1[S:23][C:22]2[C:17](=[N:18][CH:19]=[C:20]([C:25]#[N:26])[C:21]=2Cl)[CH:16]=1>O1CCCC1>[Br:14][C:15]1[S:23][C:22]2[C:17](=[N:18][CH:19]=[C:20]([C:25]#[N:26])[C:21]=2[NH:4][C:3]2[CH:5]=[C:6]([O:10][CH3:11])[C:7]([Cl:9])=[CH:8][C:2]=2[Cl:1])[CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 14766362,4-Dichloro-5-methoxyanilineHCID 9970540HCID 9970540, compound

Product 1

HCID 10410352HCID 10410352, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,4-dichloro-5-methoxyaniline (221.8 mg, 1.16 mmol) and 60% sodium hydride (46.2 mg, 1.16 mmol) in 6 mL of tetrahydrofuran is heated at reflux for 1 hour. The solution is cooled and 2-bromo-7-chlorothieno[3,2-b]pyridine-6-carbonitrile (150 mg, 0.55 mmol) is added. The resulting reaction mixture is heated at reflux for 5 hours, cooled to room temperature, and then partitioned between dichloromethane and water. The organic layer is washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by preparative thin layer chromatography developing with 40% ethyl acetate in hexane to provide 114.6 mg of 2-bromo-7-[(2,4-dichloro-5-methoxyphenyl)amino]-thieno[3,2-b]pyridine-6-carbonitrile as a white solid, mp 228-229° C.; 1H NMR (DMSO-d6) δ 3.86 (s, 3H), 7.40 (s, 1H), 7.71 (s, 1H), 7.80 (s, 1H), 8.61 (s, 1H), 9.80 (s, 1H); MS 426.0, 428.0 (M−H)−.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. temperatureThe solution is cooled
  4. customThe resulting reaction mixture
  5. temperatureis heated
  6. temperatureat reflux for 5 hours
  7. custompartitioned between dichloromethane and water
  8. washThe organic layer is washed with saturated aqueous sodium chloride
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue is purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-2910a8572f0645b98d20e675b0378707
Source dataset
uspto-grants-2006_01
Patent number
US06987116B2

Reaction notes

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