N-Iodosuccinimide → (4-fluoro-phenyl)-(3-iodo-2-phenoxymethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-5-yl)-methanone

HRID 2369609Notes

Reaction equation

[I:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:34]=[CH:33][C:13]([C:14]([N:16]2[CH2:21][CH2:20][N:19]3[N:22]=[C:23]([CH2:25][O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:24]=[C:18]3[CH2:17]2)=[O:15])=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[F:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([N:16]2[CH2:21][CH2:20][N:19]3[N:22]=[C:23]([CH2:25][O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:24]([I:1])=[C:18]3[CH2:17]2)=[O:15])=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 65 °C

Procedure

N-iodosuccinimide (70 mg, 0.31 mmol) was added to a solution of 5-(4-fluorobenzoyl)-4,5,6,7-tetrahydro-2-(phenoxymethyl)-pyrazolo[1,5-a]pyrazine (0.1 g, 0.28 mmol) in chloroform (1 mL). The mixture was stirred at 65° C. for 1 hour. Then the solvent was evaporated in vacuo and the crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo to yield (4-fluoro-phenyl)-(3-iodo-2-phenoxymethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-5-yl)-methanone (0.13 g, 96% yield) as a white solid.

Workup

customThen the solvent was evaporated in vacuo
customthe crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 50/50)
customThe desired fractions were collected
customthe solvents evaporated in vacuo

Sources & evidence

ORD record: ord-e71c97b1cc914375b085564a087e5909
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703946B2

Reaction notes

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