Ethyl orthoformate → Ethyl 4-(6-bromo-1H-benzo[d]imidazol-1-yl)-2-fluoro-benzoate

HRID 1792482Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([F:21])[CH:11]=1.[CH2:22](OC(OCC)OCC)C>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[CH:22][N:9]([C:10]3[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([F:21])[CH:11]=3)[C:3]=2[CH:4]=1

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 22031624Ethyl 4-(2-amino-5-bromo-phenylamino)-2-fluoro-benzoate

Product 1

HCID 22032273Ethyl 4-(6-bromo-1H-benzo[d]imidazol-1-yl)-2-fluoro-benzoate

Procedure

917 mg ethyl 4-(2-amino-5-bromo-phenylamino)-2-fluoro-benzoate (compound in Production Example 333) and 7 mL triethoxymethane were stirred at 140° C. for 3 hours. The solvent was evaporated, and the residue was purified by NH silica gel chromatography (ethyl acetate/hexane). By recrystallization from ethyl acetate/hexane, 734 mg of the title compound was obtained as pale pink crystals.

Workup

customThe solvent was evaporated
customthe residue was purified by NH silica gel chromatography (ethyl acetate/hexane)
customBy recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record: ord-a61b24039bde45f7abef76817ce1bb39
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074801B1

Reaction notes

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