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Methyl iodide → 1,4-Dimethyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid methyl ester

HRID 1517061
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HRID 1517061 반응식
[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[N:6][C:5]=1[OH:21].[CH3:23]OC(C1C(=O)NC(C2C=CC=C(C(F)(F)F)C=2)=CC=1C)=O.C(=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1[C:5](=[O:21])[N:6]([CH3:23])[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[CH:12]=2)=[CH:8][C:9]=1[CH3:10])=[O:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178497666HCID 178497666, 화합물

생성물 1

HCID 574411311,4-Dimethyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid methyl ester수율 33%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 0.62 g (2.0 mmol) of 2-hydroxy-4-methyl-6-(3-trifluoromethyl-phenyl)-nicotinic acid methyl ester/4-methyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid methyl ester in 20 ml of DMF was treated with 0.78 g (2.4 mmol) of cesium carbonate, followed by 0.62 ml=1.41 g (10.0 mmol) of iodomethane. This mixture was stirred for 70 hours at RT, then poured into crashed ice and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (heptane/EtOAc 4:1 to 0:1) to give 0.21 g (33%) of the title compound as light yellow solid; [MS: 326.1 (MH+)] and 0.42 g (65%) of 2-methoxy-4-methyl-6-(3-trifluoromethyl-phenyl)-nicotinic acid methyl ester as light yellow oil. MS: 326.1 (MH+).

후처리

  1. additionpoured
  2. extractionextracted twice with CH2Cl2
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (heptane/EtOAc 4:1 to 0:1)

출처 및 근거

ORD 기록
ord-420e0977df734269a31b83d634e09a23
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08227613B2

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