Pyridine → 2,3,4,5,6-Pentafluorophenyl 4-(4-bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate

HRID 917753노트

반응식

HRID 917753 반응식
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([NH:6][C:7]2[C:8]([C:15]([OH:17])=[O:16])=[CH:9][N:10]([CH3:14])[C:11](=[O:13])[CH:12]=2)=[C:4]([F:20])[CH:3]=1.FC(F)(F)C(O[C:26]1[C:31]([F:32])=[C:30]([F:33])[C:29]([F:34])=[C:28]([F:35])[C:27]=1[F:36])=O.N1C=CC=CC=1>C1COCC1>[Br:1][C:2]1[CH:19]=[CH:18][C:5]([NH:6][C:7]2[C:8]([C:15]([O:17][C:26]3[C:27]([F:36])=[C:28]([F:35])[C:29]([F:34])=[C:30]([F:33])[C:31]=3[F:32])=[O:16])=[CH:9][N:10]([CH3:14])[C:11](=[O:13])[CH:12]=2)=[C:4]([F:20])[CH:3]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 115809254-(4-Bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

생성물 1

HCID 589628492,3,4,5,6-Pentafluorophenyl 4-(4-bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate수율 97%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-(4-Bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid and pentafluorophenyl trifluoroacetate were reacted in the presence of pyridine in THF as for example 4, step A. The crude residue was purified by flash chromatography on silica gel (60% EtOAc/Hexane) to give 2,3,4,5,6-pentafluorophenyl 4-(4-bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate (97%). 1H NMR [400 MHz, (CD3)2SO] δ 9.03 (s, 1H), 8.70 (s, 1H), 7.71 (dd, J=10.6, 2.0 Hz, 1H), 7.49 (dd, J=8.5, 2.0 Hz, 1H), 7.46 (t, J=8.7 Hz, 1H), 5.34 (d, J=1.6 Hz, 1H), 3.49 (s, 3H).

후처리

  1. customThe crude residue was purified by flash chromatography on silica gel (60% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-e6bb761702a74ddd9f639b912a740ddb
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273877B2

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