4-Bromo-2-fluoroaniline → HCID 21701561, compound

HRID 1596261Notes

Reaction equation

HRID 1596261 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1.[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[C:20]([F:25])[CH:19]=1>C(O)(C)C>[ClH:2].[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:3]2[C:12]3[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=[CH:5][N:4]=2)=[C:20]([F:25])[CH:19]=1

Participants

4

Reactant 2

HCID 1230504-Bromo-2-fluoroanilineHCID 220221614-Chloro-6,7-dimethoxyquinazoline hydrochloride

Product 1

HCID 21701561HCID 21701561, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-6,7-dimethoxyquinazoline hydrochloride (130 mg, 0.5 mmol), (prepared as described for the starting material in Example 2), and 4-bromo-2-fluoroaniline (95 mg, 0.5 mmol) in isopropanol (7 ml) was heated at reflux for 2 hours. The mixture was allowed to cool to ambient temperature, the precipitated solid was collected by filtration, washed with isopropanol and ether and dried to give 4-(4-bromo-2-fluoroanilino)-6,7-dimethoxyquinazoline hydrochloride (124 mg, 60%) as an off-white solid. HPLC characteristics:

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 2 hours
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with isopropanol and ether
  6. customdried

Sources & evidence

ORD record
ord-affd7062b8934bb7a24f16561c7b9c02
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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