Methyl iodide → 5-Biphenyl-4-yl-6-fluoro-2-methylsulfanyl-1H-benzoimidazole

HRID 1960133Notes

Reaction equation

[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:16]([F:17])=[CH:15][C:10]3[NH:11][C:12](=[S:14])[NH:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.[CH2:24](N(CC)CC)C.CI>C1COCC1>[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:16]([F:17])=[CH:15][C:10]3[NH:11][C:12]([S:14][CH3:24])=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 13-4 (2.23 g, 6.9 mmol) in 40 mL of THF was added triethylamine (2.2 mL), followed by the dropwise addition of methyliodide (0.43 mL, 6.9 mmol). The reaction mixture was heated to 40° C. for 2 h. The solvent was then removed in vacuo and the residue was taken up in EtOAc and washed two times with 100 mL portions of saturated aqueous ammonium chloride and a 100 mL portion of brine. The combined organic layers were dried over MgSO4 filtered and concentrated to dryness in vacuo. Then 150 mL of CH2Cl2 were added and the resulting precipitate was collected by vacuum filtration to give title compound 13-5.

Workup

customThe solvent was then removed in vacuo
washwashed two times with 100 mL portions of saturated aqueous ammonium chloride
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated to dryness in vacuo
additionThen 150 mL of CH2Cl2 were added
filtrationthe resulting precipitate was collected by vacuum filtration

Sources & evidence

ORD record: ord-a1c9fa97de544db7967a9e34f385e707
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410284B2

Reaction notes

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