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

HRID 2112815ノート

反応式

HRID 2112815 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒

反応条件

温度
95 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-71ebb7b0966f4d7091831028c77deaf4
出典データセット
uspto-grants-2009_04
特許番号
US07524862B2

反応ノート

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