Pyridine → 4-bromomethyl-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one

HRID 982810

反応式

HRID 982810 の反応式
C1([N:4]2[C:9](=[O:10])[C:8]([CH2:11]O)=[C:7](C)[C:6]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([F:22])[CH:15]=3)=[N:5]2)CC1.C(Br)(Br)(Br)[Br:24].N1[CH:33]=[CH:32][CH:31]=[CH:30]C=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:24][CH2:11][C:8]1[C:9](=[O:10])[N:4]([CH2:30][CH:31]2[CH2:33][CH2:32]2)[N:5]=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([F:22])[CH:15]=2)[CH:7]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 672144772-Cyclopropyl-methyl-6-(3-fluoro-4-methoxyphenyl)-4-hydroxymethyl-2H-pyridazin-3-one

生成物 1

HCID 219917104-bromomethyl-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one収率 69.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2-Cyclopropyl-methyl-6-(3-fluoro-4-methoxyphenyl)-4-hydroxymethyl-2H-pyridazin-3-one (185 mg, 0.61 mmol), carbon tetrabromide (404 mg, 1.2 mmol) and pyridine (48 mg, 0.61 mmol) were dissolved in tetrahydrofuran (3 mL), and under ice-cold stirring, a solution of triphenylphosphine (319 mg, 1.2 mmol) in tetrahydrofuran (3 mL) was added. Under ice cooling, the mixture was stirred for 1 hour, and further stirred overnight at room temperature. Insoluble materials were filtered off, the solvent was distilled off under reduced pressure, and the residue was isolated and purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to yield the title compound as a yellow powder (yield: 155 mg, 69.5%).

後処理

  1. customfurther stirred overnight
  2. customat room temperature
  3. filtrationInsoluble materials were filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was isolated
  6. custompurified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

出典と根拠

ORDレコード
ord-b69529cf00c54952a4b57eefdcdaaa78
出典データセット
uspto-grants-2005_03
特許番号
US06861428B2

関連ノート

読み込み中…