Iodine → HCID 44553562, compound

HRID 1254039Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12](C3CCCCC3)=[N:11][C:10]=2[C:21]2[CH:26]=[CH:25][C:24](S(C)(=O)=O)=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.[Li+].CC([N-:35][CH:36](C)C)C.[I:39]I>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([I:39])=[N:11][C:10]=2[C:21]2[CH:26]=[CH:25][C:24]([C:36]#[N:35])=[CH:23][CH:22]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To 4-{5-[(4-chlorophenyl)thio]-1-methyl-1H-imidazol-4-yl}benzonitrile (Example 31, 50 mg, 0.153 mmol) in THF (0.75 mL) was added freshly made LDA (0.2 mL, 0.2 mmol) at −78° C. After stirring at −78° C. for 1 h, I2 (55 mg, 0.215 mmol) was added and the reaction was warmed up to rt and stirred overnight. The reaction was quenched with aq NH4Cl, and the product was extracted with EtOAc. The combined extracts were washed with aq Na2S2O3, water, and brine, dried over MgSO4, filtered, and concentrated. The residue was purified by silica column chromatography (5-20% EtOAc in hexanes) to give the title compound. 1H NMR (500 MHz, (CDCl3): 8.20 (d, 2H), 7.65 (d, 2H), 7.28 (d, 2H), 6.99 (d, 2H), 3.62 (s, 3H). LCMS: [M+1]=451.9.

Workup

temperaturethe reaction was warmed up to rt
stirringstirred overnight
customThe reaction was quenched with aq NH4Cl
extractionthe product was extracted with EtOAc
washThe combined extracts were washed with aq Na2S2O3, water, and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica column chromatography (5-20% EtOAc in hexanes)

Sources & evidence

ORD record: ord-9b35546a41ac4690b0976de9efccffb5
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455528B2

Reaction notes

Loading…