Boron tribromide → HCID 11460340, compound

HRID 2381020Notes

Reaction equation

HRID 2381020 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.B(Br)(Br)Br>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 117381122-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine

Product 1

HCID 11460340HCID 11460340, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of (2-chloro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine (100 mg, 0.334 mmol) in 30 ml dichloromethane cooled at −20° C. was added slowly 60 μl of BBr3 (0.668 mmol). The reaction mixture was stirred at −20° C. for 2 h then it was warmed to room temperature. It was stirred another 2 h at this temperature. The reaction mixture was diluted with ethyl acetate (50 ml) and washed with cold 5% sodium bicarbonate. The organic phase was dried and concentrated. The residue was purified by a small silica column using ethyl acetate and hexane (1:3) as eluents to give the product (57 mg, 57%). 1H NMR (CDCl3): 7.65-7.56 (m, 2H), 7.04-6.87 (m, 5H), 3.59 (s, 3H).

Workup

  1. temperatureit was warmed to room temperature
  2. stirringIt was stirred another 2 h at this temperature
  3. washwashed with cold 5% sodium bicarbonate
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customThe residue was purified by a small silica column

Sources & evidence

ORD record
ord-891298802cf44227899400c25664521a
Source dataset
uspto-grants-2012_09
Patent number
US08258145B2

Reaction notes

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