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

HRID 982810
Notes
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Reaction equation

HRID 982810 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-b69529cf00c54952a4b57eefdcdaaa78
Source dataset
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06861428B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes