Ammonium Chloride → 4-Fluoro-2-[1-(4-methoxy-benzyl)-1h-benzotriazol-4-yloxy]-benzoic acid methyl ester

HRID 573151Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:11]=3[N:10]=[N:9]2)=[CH:5][CH:4]=1.F[C:21]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24].CC(C)([O-])C.[K+].[Cl-].[NH4+]>COCCOCCOC>[CH3:26][O:25][C:23](=[O:24])[C:22]1[CH:21]=[CH:30][C:29]([F:31])=[CH:28][C:27]=1[O:17][C:16]1[C:11]2[N:10]=[N:9][N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=3)[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of EXAMPLE 342C (990 mg) and methyl 2,4-difluorobenzoate (734 mg) in diglyme (40 mL) was added potassium tert-butoxide (1M in tetrahydrofuran, 4.07 mL). The solution was heated to 100° C. for 16 hours, cooled, added to saturated ammonium chloride, and extracted with 70% ethyl acetate in hexanes. The extract was washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated and purified by flash column chromatography on silica gel using 30% ethyl acetate in hexanes.

Workup

temperaturecooled
extractionextracted with 70% ethyl acetate in hexanes
washThe extract was washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
custompurified by flash column chromatography on silica gel using 30% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-e75281788224416f80c449e9862d06cc
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029404B2

Reaction notes

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