1,1-Dichloroethane → HCID 90409693, compound

Reaction equation

[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C:9]1[C:14]([F:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19](Cl)=[C:18]([F:23])[CH:17]=2)[N:12]=[C:11]([C:24]([O:26][CH3:27])=[O:25])[C:10]=1[Cl:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.[Cl:43]C(Cl)C>>[C:1]([O:5][C:6]([NH:8][C:9]1[C:14]([F:15])=[C:13]([C:16]2([Cl:43])[CH:21]=[CH:20][CH:19]=[C:18]([F:23])[CH2:17]2)[N:12]=[C:11]([C:24]([O:26][CH3:27])=[O:25])[C:10]=1[Cl:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 63651,1-Dichloroethane

HCID 6422Trifluoroacetic acid

HCID 90409505HCID 90409505, compound

Product 1

HCID 90409693HCID 90409693, compoundYield 98%

Procedure

Methyl 4-(bis(tert-butoxycarbonyl)amino)-3-chloro-6-(4-chloro-3-fluorophenyl)-5-fluoropicolinate (2.1 g, 3.94 mmol) was dissolved in dichloroethane (20 mL) and trifluoroacetic acid (0.598 mL, 7.76 mmol) was added at rt. The reaction mixture was stirred overnight at room temperature then concentrated under vacuum. The product was purified by flash chromatography (SiO2, eluting with 2-20% ethyl acetate in dichloromethane) to provide the title compound as a white solid (1.64 g, 98%): 1H NMR (300 MHz, CDCl3) δ 7.80 (dd, J=22.0, 8.5 Hz, 2H), 7.50 (dd, J=8.3, 7.6 Hz, 1H), 6.51 (s, 1H), 4.02 (s, 3H), 1.56 (s, 9H); ESIMS m/z 431 ([M−H]−).