Diethyl Ether → HCID 10364922, compound

HRID 1611545Notes

Reaction equation

HRID 1611545 reaction equation
[O:1]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1.[Br:22][CH:23]1[S:31][C:30]2[C:25]([N:26](Cl)[CH:27]=[C:28]([C:32]#[N:33])[CH:29]=2)=[CH:24]1.C(OCC)C>C(OCCO)C>[Br:22][C:23]1[S:31][C:30]2[C:25](=[N:26][CH:27]=[C:28]([C:32]#[N:33])[C:29]=2[NH:12][C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:14][CH:13]=2)[CH:24]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8764(4-Aminophenoxy)benzeneHCID 10176127Pyridinium chlorideHCID 22256666HCID 22256666, compound

Product 1

HCID 10364922HCID 10364922, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 4-phenoxyaniline (430 mg, 2.32 mmol), pyridine hydrochloride (244 mg, 2.11 mmol) and 2-bromo-4-chlorothieno[3,2-b]pyridine-6-carbonitrile (578 mg, 2.11 mmol) in 10 mL of 2-ethoxyethanol is heated at 125° C. for 4 hours. The mixture is poured into diethyl ether and the solids are collected by filtration. The solids are stirred with saturated aqueous sodium bicarbonate for 1 hour. The solids are collected by filtration, washed with water and diethyl ether to give 717 mg of 2-bromo-7-[(4-phenoxyphenyl)amino]thieno[3,2-b]pyridine-6-carbonitrile as a tan solid, mp 248-250° C.; 1H NMR (DMSO-d6) δ 7.01-7.19 (m, 5H), 7.23-7.47 (m, 4H), 7.66 (s, 1H), 8.57 (s, 1H), 9.62 (s, 1H); MS 422.1, 424.1 (M+H)+.

Workup

  1. filtrationthe solids are collected by filtration
  2. filtrationThe solids are collected by filtration
  3. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-392e74d4008240ffaa0168ee95c33561
Source dataset
uspto-grants-2006_01
Patent number
US06987116B2

Reaction notes

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