Phosphorus oxide (P4O10) → 2-Bromo-6-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-4-methylquinoline

HRID 2112815Notes

Reaction equation

HRID 2112815 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:23]=[CH:24][C:25]([C:28]#[C:29][C:30]3[CH:31]=[C:32]4[C:37](=[CH:38][CH:39]=3)[NH:36][C:35](=O)[CH:34]=[C:33]4[CH3:41])=[N:26][CH:27]=2)=[CH:18][CH:17]=1.[Br:42]Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:42][C:35]1[CH:34]=[C:33]([CH3:41])[C:32]2[C:37](=[CH:38][CH:39]=[C:30]([C:29]#[C:28][C:25]3[CH:24]=[CH:23][C:22]([C:19]4[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=4)=[CH:27][N:26]=3)[CH:31]=2)[N:36]=1

Participants

6

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 61697BROMINE CHLORIDE (BrCl)2×HCID 690669966-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-4-methyl-1H-quinolin-2-one

Product 1

HCID 860798522-Bromo-6-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-4-methylquinoline

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

478 mg (1.48 mmol) of tetrabutylammonium bromide and 493 mg (3.37 mmol) of phosphorus pentoxide are added to a suspension of 500 mg (1.21 mmol) of 6-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-4-methyl-1H-quinolin-2-one in 10 mL of toluene and the reaction mixture is heated to 95° C. for 1.5 hours. After cooling, the organic phase is decanted off, the residue is treated twice with toluene in the ultrasound bath, and the combined organic phases are washed with semisaturated sodium bicarbonate solution and water and dried over magnesium sulfate. After the desiccant and solvent have been eliminated, the residue is dried and reacted further without purification. Yield: 120 mg (18% of theoretical); C23H14BrClN2 (M=433.730); calc.: molpeak (M+H)+: 433/435/437 (BrCl); found: molpeak (M+H)+: 433/435/437 (BrCl).

Workup

  1. temperatureAfter cooling
  2. customthe organic phase is decanted off
  3. additionthe residue is treated twice with toluene in the ultrasound bath
  4. washthe combined organic phases are washed with semisaturated sodium bicarbonate solution and water
  5. dry with materialdried over magnesium sulfate
  6. customthe residue is dried
  7. customreacted further without purification

Sources & evidence

ORD record
ord-71ebb7b0966f4d7091831028c77deaf4
Source dataset
uspto-grants-2009_04
Patent number
US07524862B2

Reaction notes

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