4-Bromo-2,6-difluoroaniline → HCID 21260300, compound

HRID 634666Notes

Reaction equation

HRID 634666 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]=[C:23]([F:25])[C:21]([NH2:22])=[C:20]([F:26])[CH:19]=1>C(O)(C)C>[ClH:2].[Br:17][C:18]1[CH:24]=[C:23]([F:25])[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:26])[CH:19]=1

Participants

4

Reactant 2

HCID 6101914-Bromo-2,6-difluoroanilineHCID 220221614-Chloro-6,7-dimethoxyquinazoline hydrochloride

Product 1

HCID 21260300HCID 21260300, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-6,7-dimethoxyquinazoline hydrochloride, (152 mg, 0.6 mmol), (prepared as described for the starting material in Example 1 but without the aqueous work up), and 4-bromo-2,6-difluoroaniline (121 mg, 0.6 mmol) in isopropanol (7 ml) was heated at reflux for 2 hours. The mixture was allowed to cool, the solid product collected by filtration, washed with isopropanol and dried to give 4-(4-bromo-2,6-difluoroanilino)-6,7-dimethoxyquinazoline hydrochloride (81 mg, 35%).

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 2 hours
  4. temperatureto cool
  5. filtrationthe solid product collected by filtration
  6. washwashed with isopropanol
  7. customdried

Sources & evidence

ORD record
ord-d0563b6d38e84c578deff83e828b50c7
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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