* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Step 3 :; [0109] To a solution of methyl 4, 5-difluoro-2-nitrobenzoate Ib (23.0 g, 106 mmol) in EtOAc (200 mL), was added 10percent Pd/C (wet, 50 percent water, 6.0 g), and the mixture was shaken on a Parr hydrogenator at 50 PSI for 3 hr. The reaction mixture was then filtered through a celite pad and the filtrate was concentrated by rotary evaporation to yield methyl 2-amino-4, 5-difluorobenzoate Ic as a colorless solid, 19.Og (96percent).
Procedure H: TMSCH2N2-mediated esterification (Exemplified by 31e)TMSCH2N2 (1.9 mL, 3.82 mmol, 2.0 M in hexanes) was added to a stirred solution of the aminobenzoic acid (600 mg, 3.47 mmol) in 20 mL of DCM:MeOH (9:1) under nitrogen atmosphere at room temperature. After 30 min, the reaction mixture was quenched by glacial HO Ac before being diluted with DCM and washed with NaHC03 (aq., sat.). The organic phase was dried over Na2S04, filtered, and concentrated to give the methyl aminobenzoate in 99percent yield (644 mg).; 2-[2-(2-fluorobenzoylamino)-benzoylamino]-4,5-difluorobenzoic acid - Compound 35e35a was synthesized by procedures H, A, E, A, and C.
99%
With methanol In hexane; dichloromethane at 20℃; for 0.5 h; Inert atmosphere
Procedure H: TMSCH2N2-Mediated Esterification (Exemplified by 31e) TMSCH2N2 (1.9 mL, 3.82 mmol, 2.0 M in hexanes) was added to a stirred solution of the aminobenzoic acid (600 mg, 3.47 mmol) in 20 mL of DCM:MeOH (9:1) under nitrogen atmosphere at room temperature. After 30 min, the reaction mixture was quenched by glacial HOAc before being diluted with DCM and washed with NaHCO3 (aq., sat.). The organic phase was dried over Na2SO4, filtered, and concentrated to give the methyl aminobenzoate in 99percent yield (644 mg).
Reference：
[1] Patent: WO2011/155898, 2011, A1, . Location in patent: Page/Page column 52; 58
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3170 - 3181
[3] Patent: US2013/210915, 2013, A1, . Location in patent: Paragraph 0302
3
[ 32315-10-9 ]
[ 83506-93-8 ]
[ 207346-42-7 ]
Reference：
[1] Patent: US6413724, 2002, B1,
4
[ 67-56-1 ]
[ 83506-93-8 ]
[ 207346-42-7 ]
Reference：
[1] Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 1, p. 64 - 69
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