Water → 8-(2,4-Dichlorophenyl)-4-(4-isopropyloxycarbonyl-1,2,3,6-tetrahydropyridin-1-yl)-2-methylquinoline

HRID 1373095

反応式

HRID 1373095 の反応式
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[C:7]2[N:13]1[CH2:18][CH:17]=[C:16]([C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1OB(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C.C1(C)C=CC=CC=1>[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[C:7]2[N:13]1[CH2:18][CH:17]=[C:16]([C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1

参加物

8

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 219844772,4-Dichlorophenylboric acidHCID 225744308-Bromo-4-(4-isopropyloxycarbonyl-1,2,3,6-tetrahydropyridin-1-yl)-2-methylquinoline

生成物 1

HCID 121346738-(2,4-Dichlorophenyl)-4-(4-isopropyloxycarbonyl-1,2,3,6-tetrahydropyridin-1-yl)-2-methylquinoline収率 76.8%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

Under a nitrogen atmosphere, 8-bromo-4-(4-isopropyloxycarbonyl-1,2,3,6-tetrahydropyridin-1-yl)-2-methylquinoline (5.9 g), 2,4-dichlorophenylboric acid (3.2 g) and sodium carbonate (4.8 g) were suspended in a mixed solvent of deaerated water (15 mL), toluene (7.5 mL) and ethanol (7.5 mL), followed by adding thereto tetrakis(triphenylphosphine)palladium (0.88 g), and the resulting mixture was heated under reflux for 5 hours. The reaction mixture was cooled to room temperature to be separated. After the aqueous phase was extracted with ethyl acetate, the combined organic phase was dried over anhydrous sodium sulfate. The desiccating agent was filtered off, after which the filtrate was concentrated under reduced pressure and the resultant residue was crystallized from diisopropyl ether. The crystals were collected by filtration and washed with a small amount of diisopropyl ether to obtain the title compound (5.3 g).

後処理

  1. additionby adding
  2. temperatureunder reflux for 5 hours
  3. customto be separated
  4. extractionAfter the aqueous phase was extracted with ethyl acetate
  5. dry with materialthe combined organic phase was dried over anhydrous sodium sulfate
  6. filtrationThe desiccating agent was filtered off
  7. concentrationafter which the filtrate was concentrated under reduced pressure
  8. customthe resultant residue was crystallized from diisopropyl ether
  9. filtrationThe crystals were collected by filtration
  10. washwashed with a small amount of diisopropyl ether

出典と根拠

ORDレコード
ord-06c272ecfe43434a9a4f2ca58aa658d1
出典データセット
uspto-grants-2007_01
特許番号
US07160900B2

関連ノート

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