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

HRID 8038

Reaction equation

HRID 8038 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

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-75f5140c9d8a44fa82529fda053a0ac4
Source dataset
uspto-grants-2006_08
Patent number
US07087606B2

Linked notes

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