4-Chloro-6-iodoquinazoline → N-(4-(3-fluorobenzyloxy)-3-bromophenyl)-6-iodoquinazolin-4-amine

HRID 877103Notes

Reaction equation

HRID 877103 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[Br:14].Cl[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([I:29])[CH:27]=2)[N:22]=[CH:21][N:20]=1>C(O)(C)C>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([I:29])[CH:27]=3)[N:22]=[CH:21][N:20]=2)=[CH:9][C:8]=1[Br:14]

Participants

4

Reactant 2

HCID 111738094-Chloro-6-iodoquinazolineHCID 218747953-Bromo-4-[(3-fluorophenyl)methoxy]aniline

Product 1

HCID 21874791N-(4-(3-fluorobenzyloxy)-3-bromophenyl)-6-iodoquinazolin-4-amineYield 98.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-(3-fluorobenzyloxy)-3-bromobenzenamine (1.48 g, 5 mmol) and 4-chloro-6-iodo-quinazoline (1.45 g, 5 mmol) were dissolved in isopropanol (50 ml). The reaction mixture was refluxed for 12 hours. The solid product was collected by filtration, washed with cold isopropanol (10 mL) and ether (20 mL), and air dried to afford 2.7 g of the clean desired material.

Workup

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. filtrationThe solid product was collected by filtration
  3. washwashed with cold isopropanol (10 mL) and ether (20 mL), and air
  4. customdried

Sources & evidence

ORD record
ord-68d56f6fe58e4445beab4fc9980a6fed
Source dataset
uspto-grants-2015_03
Patent number
US08987284B2

Reaction notes

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