Water → (4-Chloro-8-trifluoromethyl-quinolin-3-yl)-pyridin-2-yl-methanone

HRID 2104476

反応式

HRID 2104476 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.C(O[C:16]([C:18]1[CH:19]=[N:20][C:21]2[C:26]([C:27]=1[Cl:28])=[CH:25][CH:24]=[CH:23][C:22]=2[C:29]([F:32])([F:31])[F:30])=[O:17])C.O>C1COCC1>[Cl:28][C:27]1[C:26]2[C:21](=[C:22]([C:29]([F:30])([F:31])[F:32])[CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19][C:18]=1[C:16]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)=[O:17]

参加物

6

反応物 4

HCID 962WaterHCID 79732-BromopyridineHCID 725465Ethyl 4-chloro-8-(trifluoromethyl)quinoline-3-carboxylateHCID 178418339Butyllithium

生成物 1

HCID 66913162(4-Chloro-8-trifluoromethyl-quinolin-3-yl)-pyridin-2-yl-methanone収率 37.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

2-Bromopyridine (0.74 mL, 7.90 mmol) was taken into THF (30 mL) and cooled to −78° C. Then BuLi (4.8 mL, 7.90 mmol, 1.6 M solution in hexane) was added dropwise and then stirred for 30 minutes. Next, 4-Chloro-8-(trifluoromethyl)-3-quinolinecarboxylic acid ethyl ester (2.0 g, 6.58 mmol) in THF (10 mL) was added rapidly and stirred at −78° C. for 4 hours. The reaction was poured into water/saturated NH4Cl solution and then extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated. The resulting material was purified via column chromatography using 15% ethyl acetate in hexane as the eluent to yield 0.823 g of (4-chloro-8-trifluoromethyl-quinolin-3-yl)-pyridin-2-yl-methanone as a yellow solid.

後処理

  1. stirringstirred at −78° C. for 4 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting material was purified via column chromatography

出典と根拠

ORDレコード
ord-1c791553cc134315ab75db10bb4b34e4
出典データセット
uspto-grants-2009_08
特許番号
US07576215B2

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