3,4,5-Trimethoxyaniline → HCID 10344502, compound

HRID 1611544Notes

Reaction equation

HRID 1611544 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[NH2:6].Cl.N1C=CC=CC=1.Cl[N:22]1[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[C:24]2[S:30][CH:31]([I:33])[CH:32]=[C:23]12.C(=O)(O)[O-].[Na+]>C(OCCO)C>[I:33][C:31]1[S:30][C:24]2[C:23](=[N:22][CH:27]=[C:26]([C:28]#[N:29])[C:25]=2[NH:6][C:5]2[CH:7]=[C:8]([O:12][CH3:13])[C:9]([O:10][CH3:11])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:32]=1

Participants

6

Reactant 4

HCID 322853,4,5-TrimethoxyanilineHCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 22256673HCID 22256673, compound

Product 1

HCID 10344502HCID 10344502, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 3,4,5-trimethoxyaniline (964 mg, 5.26 mmol), pyridine hydrochloride (100 mg, 0.76 mmol) and 4-chloro-2-iodothieno[3,2-b]pyridine-6-carbonitrile (937 mg, 2.92 mmol) in 50 mL of 2-ethoxyethanol is heated at reflux overnight. The solution is poured into saturated aqueous sodium bicarbonate and the resulting solid is collected by filtration, washed with water and dried under reduced pressure. The resultant solid is purified by flash column chromatography eluting with 2% methanol in dichloromethane. The fractions containing product are combined and concentrated to provide 1.17 g of 2-iodo-7-[(3,4,5-trimethoxyphenyl)amino]thieno[3,2-b]pyridine-6-carbonitrile as white crystals, mp 254-256° C.; 1H NMR (DMSO-d6) δ 3.70-3.78 (m, 9H), 6.66 (s, 2H), 7.72 (s, 1H), 8.53 (s, 1H), 9.56 (s, 1H); MS 468.1 (M+H)+.

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. filtrationthe resulting solid is collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure
  6. customThe resultant solid is purified by flash column chromatography
  7. washeluting with 2% methanol in dichloromethane
  8. additionThe fractions containing product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d5e2c3ef95344fb4b4ac54ce9d82bc9a
Source dataset
uspto-grants-2006_01
Patent number
US06987116B2

Reaction notes

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