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

HRID 2112815노트

반응식

HRID 2112815 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매

반응 조건

온도
95 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-71ebb7b0966f4d7091831028c77deaf4
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07524862B2

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