methyl 7-fluoro-6-(phenylamino)-3H-benzo[d]imidazole-5-carboxylate synthesis

7synthesis methods

Product Name:methyl 7-fluoro-6-(phenylamino)-3H-benzo[d]imidazole-5-carboxylate
CAS Number:606093-59-8
Molecular formula:C15H12FN3O2
Molecular Weight:285.27

64-18-6 Synthesis

64-18-6
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Methyl 4-Amino-3-Fluoro-5-Nitro-2-(Phenylamino)Benzoate

606093-58-7
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methyl 7-fluoro-6-(phenylamino)-3H-benzo[d]imidazole-5-carboxylate

606093-59-8
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Yield:606093-59-8 86%

Reaction Conditions:

palladium(II) hydroxide/carbon in ethanol at 40 - 95; for 18 h;

Steps:

1B.E

4-Amino-3-fluoro-5-nitro-2-phenylamino-benzoic acid methyl ester (16.70 g, 54.71 mmol), formic acid (250 ml, 6.63 mol) and 20% Pd(OH)₂/C (9.00 g, 16.91 mmol) in ethanol (250 mL) were stirred at 40 ⁰C for two hours under N₂ and then at 95⁰C for 16 hours. The reaction mixture was cooled to room temperature and filtered through Celite rinsing with ethyl acetate. The filtrate was concentrated under reduced pressure to give a yellow solid. The solid was triturated with diethyl ether to give 13.47 g (86%) of the desired product as a tan solid. MS APCI (+) M/Z 286 (M+ 1) detected; MS APCI (-) m/z 284 (M-I) detected.

References:

WO2007/76245,2007,A2 Location in patent:Page/Page column 19

606144-42-7 Synthesis