Isopropyl 4-(amino)-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-picolinate → Methyl 4-(acetylamino)-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-picolinate
Reaction equation
NC1C(F)=C([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH3:17])[C:10]=2[F:18])N=C(C(OC(C)C)=O)C=1.[C:25]([NH:28][C:29]1[C:34]([F:35])=[C:33](Br)[N:32]=[C:31]([C:37]([O:39][CH3:40])=[O:38])[CH:30]=1)(=[O:27])[CH3:26]>>[C:25]([NH:28][C:29]1[C:34]([F:35])=[C:33]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH3:17])[C:10]=2[F:18])[N:32]=[C:31]([C:37]([O:39][CH3:40])=[O:38])[CH:30]=1)(=[O:27])[CH3:26]Participants
Procedure
Methyl 4-(acetylamino)-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-picolinate was prepared in analogous fashion to isopropyl 4-(amino)-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-picolinate in Example 10 except that methyl 4-acetamido-6-bromo-5-fluoropicolinate was used in place of isopropyl 4-amino-6-bromo-5-fluoropicolinate: mp=189-191° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.5 (s, 1H), 9.04 (d, JF-H=5.6 Hz, 1H), 7.53 (dd, J=8.4, 1.6 Hz, 1H), 7.37 (dd, J=8.4, 7.0 Hz, 1H), 3.95 (s, 3H), 3.89 (s, 3H), 2.22 (s, 3H); 13C NMR (100.6 MHz, DMSO-d6) δ 170.3, 164.1, 154.4, 151.9, 149.4, 146.7, 144.1-143.8 (m), 140.5 (d, JF-C=15.3 Hz), 135.1 (d, JF-C=10.8 Hz), 128.9 (d, JF-C=3.4 Hz), 125.9 (dd, JF-C=35.0, 3.5 Hz), 122.9 (dd, JF-C=13.7, 3.5 Hz), 61.6, 52.6, 24.1; 19F {1H} NMR (376.5 MHz, DMSO-d6) δ −129.5 (d, JF-F=27.5 Hz), −142.8 (d, JF-F=27.5 Hz); IR: 3341, 2972, 2944, 1733, 1705, 1599, 1507, 1439, 1416, 1406, 1371, 1283, 1166, 1039, 974, 926, 890, 823, 678; MS Calcd. for C16H13ClF2N2O4: 370.1. Found: 370 (M+), 312.
Sources & evidence
- ORD record
- ord-fede068058fe4a3c9a054cc1e86b74ff
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871943B2
Reaction notes
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