Ammonium Chloride → 2-(3-fluoropyridin-4-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole

HRID 1256595Notes

Reaction equation

[CH3:1][NH:2][C:3]1[C:4]([NH2:13])=[CH:5][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:8]=1.[F:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[CH:21]=O.S(=O)(O)[O-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[F:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[C:21]1[N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][C:6]([C:9]([F:10])([F:11])[F:12])=[CH:5][C:4]=2[N:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1.90 g of N1-methyl-4-trifluoromethylbenzene-1,2-diamine, 1.49 g of 3-fluoropyridine-4-carbaldehyde, 3.12 g of sodium bisulfite and 20 ml of DMF was stirred for 1.5 hours while heating at 80° C., then, was stirred for 2 hours while heating at 120° C. After cooling down to room temperature, a saturated ammonium chloride aqueous solution was poured, and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.83 g of 2-(3-fluoropyridin-4-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter, referred to as present active compound 4).

Workup

stirringwas stirred for 2 hours
temperaturewhile heating at 120° C
temperatureAfter cooling down to room temperature
extractionthe mixture was extracted three times with ethyl acetate
dry with materialThe combined organic layers were dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-1515521152354cd49d7dd40bbfb5e865
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461181B2

Reaction notes

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