Sodium hydride → HCID 10410352, compound

HRID 1178630Notes

Reaction equation

HRID 1178630 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-5797f008955242c5b29b8fa5c67aba8f
Source dataset
uspto-grants-2007_10
Patent number
US07276519B2

Reaction notes

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