2-Amino-5-fluoro-3-nitrotoluene, 2-Amino-5-fluoro-3-methyl-1-nitrobenzene

An aqueous solution of sodium hydroxide (4 mol, 229.19 ml) was added into a solution of the control example2G (34 g, 137.86 mmol) in tetrahydrofuran (5 ml), the reaction solution was heated to 95C and stirred for 2 hours; uponthe completion of the reaction, the reaction solution was cooled, into which were added ethyl acetate (50 ml) and water(50 ml), the mixture was extracted with ethyl acetate (100 ml X 5). The organic layer was combined and washed withwater (20 ml X 2) and saturated saline (10 ml) successively, dried over anhydrous sodium sulfate, filtered, and concentratedin vacuum, the residue of which was purified over a flash silica gel column to give the control example 2H (4.91g, 28.86 mmol) as a yellow solid. 1HNMR (400MHz, DMSO-d6) delta 7.65 (dd, J=2.3, 9.3 Hz, 1H), 7.39 (d, J=8.0 Hz, 1H), 7.25-7.05 (m, 1H), 2.23(s, 3H).Pd(dba)2 (169.05 mg, 294.00 mmol), XPhos (280.31 mg, 588.00 mmol) and potassium carbonate (1.22 g, 8.82mmol) were added into a solution of the control example 2H (500.00 mg, 2.94 mmol) and the control example 2E (1.32g, 3.82 mmol) in tert-butanol (5.00 ml). Under the protection of nitrogen, the suspension was heated to 110C, and stirredfor 4 hours; upon completion, the reaction was cooled, filtered, and the filtrate was concentrated in vacuum, the residueof which was purified over a flash silica gel column to give the product (2.90 g, 6.05 mmol) as a light yellow solid. 1HNMR (400MHz, CHLOROFORM-d) delta 8.55 (s, 2H), 7.75 (s, 1H), 7.62 (dd, J=2.9, 7.9 Hz, 1H), 7.31 (dd, J=2.8, 8.3 Hz, 1H), 7.09-6.87 (m, 2H), 6.54 (s, 1H), 3.95 (s, 6H), 2.36 (s, 3H). LCMS (ESI) m/z: 479.0 [M+1]+

Molecular Weight:170.14
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:170.04915563
Monoisotopic Mass:170.04915563
Topological Polar Surface Area:71.8
Heavy Atom Count:12
Complexity:183
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes