Iodine → HCID 44554077, compound

HRID 1254049Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[N:11]([CH3:21])[C:12]=2[S:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[Li]CCCC.[I:33]I>C1COCC1>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([S:13][C:12]2[N:11]([CH3:21])[C:10]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[N:9][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([I:33])=[CH:3][CH:4]=2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To 2-{4-(4-bromophenyl)-5-[(4-chlorophenyl)thio]-1-methyl-1H-imidazol-2-yl}pyridine (Example 15, 150 mg, 0.33 mmol) in THF (1 mL) was added BuLi (2.5 M in hexanes, 0.17 mL, 0.427 mmol) at −78° C. After stirring at −78° C. for 0.5 h, I2 (167 mg, 0.657 mmol) was added and the reaction was allowed to warm up to rt overnight. The reaction was quenched with aq NH4Cl, 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 gel column chromatography (1-20% EtOAc in hexanes) to give the title compound. 1H NMR (500 MHz, (CDCl3): 8.64 (d, 1H), 8.38 (d, 1H), 7.87 (d, 2H), 7.85 (t, 1H), 7.78 (d, 2H), 7.38 (t, 1H), 7.25 (d, 2H), 7.03 (d, 2H), 4.11). LCMS: [M+1]=504.

Workup

temperatureto warm up to rt overnight
customThe reaction was quenched with aq NH4Cl
extractionextracted 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 gel column chromatography (1-20% EtOAc in hexanes)

Sources & evidence

ORD record: ord-7dff34b2a565405dbbc3cd53957c54fd
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455528B2

Reaction notes

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