Iodo benzene diacetate → HCID 67234327, compound

HRID 339688Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([F:21])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](/[CH:12]=[N:13]/[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH:8]=[CH:7]2.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[N:14]1[N:13]=[C:12]([C:9]2[CH:8]=[CH:7][C:6]3[C:11](=[C:2]([Br:1])[CH:3]=[C:4]([F:21])[CH:5]=3)[N:10]=2)[N:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=12

Participants

Conditions

Temperature: 23 °C

Procedure

(E)-1-((8-Bromo-6-fluoroquinolin-2-yl)methylene)-2-(pyridin-2-yl)hydrazine (100 mg, 0.290 mmol) was weighed into a 25 mL 1 neck round bottom flask and suspended in 6.0 mL of DCM, followed by addition of iodobenzene diacetate (103 mg, 0.32 mmol). The reaction was stirred at 23° C. overnight, after which all starting materials had been consumed. The reaction was transferred to a separatory funnel and partitioned between 30 mL DCM and 30 mL Na2SO3, and the aqueous layer was washed with DCM. The combined organics were dried over magnesium sulfate and concentrated in vacuo to afford a white/yellow powder. The powder was triturated with 10 mL of anhydrous Et2O, affording the desired product as a white solid (74 mg, 74.4% yield). MS APCI (+) m/z 343 (M+1) detected.

Workup

customafter which all starting materials had been consumed
customThe reaction was transferred to a separatory funnel
custompartitioned between 30 mL DCM and 30 mL Na2SO3
washthe aqueous layer was washed with DCM
dry with materialThe combined organics were dried over magnesium sulfate
concentrationconcentrated in vacuo
customto afford a white/yellow powder
customThe powder was triturated with 10 mL of anhydrous Et2O

Sources & evidence

ORD record: ord-7101884dfe4f4f8199659556a762a080
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895550B2

Reaction notes

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