HCID 71551894, compound → Methyl 4-(acetylamino)-6-bromo-3-chloro-5-fluoro-picolinate

HRID 541041Notes

Reaction equation

HRID 541041 reaction equation
[C:1]([NH:4][C:5]1[C:10]([F:11])=[C:9](Cl)[N:8]=[C:7]([C:13]([O:15][CH3:16])=[O:14])[C:6]=1[Cl:17])(=[O:3])[CH3:2].NC1C(F)=C([Br:26])N=C(C(OC)=O)C=1Cl>>[C:1]([NH:4][C:5]1[C:10]([F:11])=[C:9]([Br:26])[N:8]=[C:7]([C:13]([O:15][CH3:16])=[O:14])[C:6]=1[Cl:17])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 71551894HCID 71551894, compoundHCID 86709862Methyl 4-acetamido-3,6-dichloro-5-fluoropicolinate

Product 1

HCID 86709863Methyl 4-(acetylamino)-6-bromo-3-chloro-5-fluoro-picolinate

Procedure

Methyl 4-(acetylamino)-6-bromo-3-chloro-5-fluoro-picolinate was prepared in analogous fashion to methyl 4-(acetylamino)-3,6-dichloro-5-fluoro-picolinate in Example 8 except that methyl 4-amino-6-bromo-3-chloro-5-fluoropicolinate was used in place of methyl 4-amino-3,6-dichloro-5-fluoropicolinate: mp=190-192° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.5 (s, 1H), 3.93 (s, 3H), 2.16 (s, 3H); 13C NMR (100.6 MHz, DMSO-d6) δ 168.0, 162.8, 153.1, 150.5, 143.7 (d, JF-C=24 Hz), 134.1 (d, JF-C=56 Hz), 127.3 (d, JF-C=96 Hz), 53.2, 22.5; 19F NMR (376.5 MHz, DMSO-d6) δ −108.3; MS Calcd. for C9H7BrCl2FN2O3: 323.93. Found: 289, 226.

Sources & evidence

ORD record
ord-f885967ad6dd47b18db93cb0c4903f27
Source dataset
uspto-grants-2014_10
Patent number
US08871943B2

Reaction notes

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