Sodium Carbonate → HCID 178506266, compound

HRID 1468095Notes

Reaction equation

[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=1B(O)O.O1CCOCC1.[Cl:19][C:20]1[C:32](I)=[CH:31][C:23]2[NH:24][C:25]([C:27]([F:30])([F:29])[F:28])=[N:26][C:22]=2[CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:19][C:20]1[C:32]([C:3]2[CH:4]=[C:5]([Cl:9])[CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])=[CH:31][C:23]2[NH:24][C:25]([C:27]([F:29])([F:30])[F:28])=[N:26][C:22]=2[CH:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Compound number 261 (i.e., 6-chloro-5-(2,3,5-trichlorophenyl)-2-trifluoromethylbenzimidazole) was prepared as follows. A 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen. (2,3,5-trichlorophenyl)boronic acid (284 mg, 1.26 mmol, 2.00 equiv), dioxane (30 mL), 5-chloro-6-iodo-2-(trifluoromethyl)-1H-1,3-benzodiazole (200 mg, 0.58 mmol, 1.00 equiv), sodium carbonate (191 mg), water (8 mL) and Pd(PPh3)4 (34.7 mg) was placed in the flask. The resulting solution was stirred overnight at 100° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:4). This resulted in 22.3 mg (10%) of 6-chloro-5-(2,3,5-trichlorophenyl)-2-trifluoromethylbenzimidazole as a white solid.

Workup

customA 100-mL round-bottom flask purged
temperaturemaintained with an inert atmosphere of nitrogen
concentrationThe resulting mixture was concentrated under vacuum
customThis resulted in 22.3 mg (10%) of 6-chloro-5-(2,3,5-trichlorophenyl)-2-trifluoromethylbenzimidazole as a white solid

Sources & evidence

ORD record: ord-ae553db97a6d413cb5c4b6589f5d6622
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000187B2

Reaction notes

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