Diethyl Ether → {(2-Methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methyl}-2-methylquinolin-5-amine

HRID 1673269

反応式

HRID 1673269 の反応式
[F:1][C:2]([F:7])([F:6])[CH:3]1[O:5][CH2:4]1.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].COC1C=CC=CC=1C=[N:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH:25]=[CH:26][C:27]([CH3:33])=[N:28]2.C(OCC)C.[CH2:39]1[CH2:43][O:42][CH2:41][CH2:40]1>CCCCCC>[CH3:41][O:42][C:43]1[CH:11]=[CH:10][CH:9]=[CH:8][C:39]=1[CH:40]([C:26]1[C:27]([CH3:33])=[N:28][C:29]2[CH:30]=[CH:31][CH:32]=[C:23]([NH2:22])[C:24]=2[CH:25]=1)[C:3]1([C:2]([F:7])([F:6])[F:1])[CH2:4][O:5]1

参加物

7

反応物 5

HCID 3283Diethyl EtherHCID 8028Tetrahydrofuran2 回HCID 5207692-(Trifluoromethyl)oxiraneHCID 67136395[1-(2-Methoxyphenyl)methylidene]-(2-methylquinolin-5-yl)amineHCID 178418339Butyllithium

生成物 1

HCID 86618227{(2-Methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methyl}-2-methylquinolin-5-amine

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒2 回

反応条件

温度
-100 °C

実験手順

To 1.74 g (11 mmol) 5-amino-2-methylquinolin and 1.33 ml (11 mmol) 2-methoxybenzaldehyde in 33 ml toluene are added 50 μl acetic acid and 2 g molecular sieve. The mixture is heated over 2 hours under reflux and filtrated through a path of cellites after cooling. The solvent is evaporated and the residue is two times azeothrophed with small portions of toluene. 3.6 g of [1-(2-methoxyphenyl)methylidene]-(2-methylquinolin-5-yl)amine are obtained as a yellow oil. 2,25 ml (26 mmol) 1,1,1-Trifluoroepoxypropane in 38 ml THF and 11 ml hexane are cooled to −100° C. and 15 ml of a 1.6 M n-butyl lithium solution in hexane are added over one hours while the temperature does not exceed −95° C. 10 Minutes after complete addition 3.6 g (11 mmol) raw [1-(2-methoxyphenyl)methylidene]-(2-methylquinolin-5-yl)amine in 49 ml THF are added over one hour while the temperature does not exceed −95° C. After one hour at −100° C. 12 ml diethyl ether are added and the reaction mixture is warmed to −100° C. over one hour. The reaction was quenched by addition of saturated ammonium chloride solution. The phases were separated and the aqueous layer was extracted twice with diethyl ether, the combined organic phases washed with brine, dried over sodium sulphate and then evaporated. Flash chromatography on silica gel (acetone in hexane 0 to 30%) yields 4.27 g {(2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methyl}-2-methylquinolin-5-amine as mixture of diastereomeres.

後処理

  1. customdoes not exceed −95° C
  2. additionare added over one hour while the temperature
  3. customdoes not exceed −95° C
  4. customThe reaction was quenched by addition of saturated ammonium chloride solution
  5. customThe phases were separated
  6. extractionthe aqueous layer was extracted twice with diethyl ether
  7. washthe combined organic phases washed with brine
  8. dry with materialdried over sodium sulphate
  9. customevaporated

出典と根拠

ORDレコード
ord-2d2ac744c72f467e8aa765c1cd63a4d5
出典データセット
uspto-grants-2011_08
特許番号
US07999108B2

関連ノート

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