Tetramethyltin → 4-Amino-6-(4-chlorophenyl)-5-fluoro-3-methylpyridine-2-carboxylic acid methyl ester

HRID 245289노트

반응식

HRID 245289 반응식
[CH3:1][O:2][C:3]([C:5]1[C:10](Cl)=[C:9]([NH2:12])[C:8]([F:13])=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[N:6]=1)=[O:4].[CH3:21][Sn](C)(C)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:10]([CH3:21])=[C:9]([NH2:12])[C:8]([F:13])=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[N:6]=1)=[O:4]

참가 물질

4

반응물 2

HCID 11661TetramethyltinHCID 22677303Methyl 4-amino-5-fluoro-3-chloro-6-(4-chlorophenyl)picolinate

생성물 1

HCID 594321264-Amino-6-(4-chlorophenyl)-5-fluoro-3-methylpyridine-2-carboxylic acid methyl ester수율 38.2%

시약·촉매·용매 1

HCID 178418476HCID 178418476, 화합물촉매

반응 조건

온도
130 °C

실험 절차

4-Amino-3-chloro-6-(4-chlorophenyl)-5-fluoropyridine-2-carboxylic acid methyl ester (0.400 g, 1.269 mmol), tetramethylstannane (3.41 g, 19.04 mmol), and bis(triphenylphosphine)palladium(II) dichloride (0.089 g, 0.127 mmol) were combined and heated to 130° C. for 25 min in a CEM microwave reactor. The cooled reaction mixture was concentrated onto silica gel and purified by flash chromatography on silica gel (ethyl acetate/hexane gradient) to yield the title compound (0.143 g, 38.2% yield): 1H NMR (CDCl3) δ 7.88 (m, 2H), 7.41 (m, 2H), 4.41 (br s, 2H), 3.96 (s, 3H), 2.36 (s, 3H).

후처리

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated onto silica gel
  3. custompurified by flash chromatography on silica gel (ethyl acetate/hexane gradient)

출처 및 근거

ORD 기록
ord-8f077e8a7925468bbdd867ead5bf3930
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658791B2

반응 노트

불러오는 중…