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

HRID 1348778

반응식

HRID 1348778 반응식
[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[C:9]([CH2:12]O)=[CH:8][C:7]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([F:22])[CH:15]=3)=[N:6]2)[CH2:3][CH2:2]1.C(Br)(Br)(Br)[Br:24].N1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:24][CH2:12][C:9]1[C:10](=[O:11])[N:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[N:6]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([F:22])[CH:15]=2)[CH:8]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 219916432-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-hydroxymethyl-2H-pyridazin-3-one

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

2-Cyclopropylmethyl-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 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%).

후처리

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

출처 및 근거

ORD 기록
ord-333717e0bb544534a877158b4bc3d3a6
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07211577B2

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