Methanol → 4-Isopropyl-2-methyl-quinolin-8-ol

HRID 1959568ノート

反応式

HRID 1959568 の反応式
[CH:1]([Li])([CH3:3])[CH3:2].Br[C:6]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([CH3:17])[CH:7]=1.CO>C1COCC1.O1CCOCC1.[Cl-].[Cl-].[Zn+2].C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH:1]([C:6]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([CH3:17])[CH:7]=1)([CH3:3])[CH3:2]

参加物

8

反応物 3

HCID 887MethanolHCID 670771594-Bromo-2-methyl-quinolin-8-olHCID 178506895HCID 178506895、化合物

生成物 1

HCID 670774524-Isopropyl-2-methyl-quinolin-8-ol

試薬・触媒・溶媒 4

HCID 3007855Zincchloride触媒HCID 11071931Dichloropalladium--(ethane-1,2-diyl)bis(diphenylphosphane) (1/1)触媒HCID 8028Tetrahydrofuran溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A solution of ZnCl2 (0.29 g, 2.1 mmol) in anhydrous THF (2.1 mL) was added dropwise to a stirred solution of isopropyllithium (0.7 M in pentane, 1.6 mL, 1.1 mmol) at −92° C. The reaction mixture was allowed to reach room temperature and was than transferred to a suspension of dichloro(1,2-bis(diphenylphosphino)ethane)palladium (II) (36 mg, 0.063 mmol) and 4-bromo-2-methyl-quinolin-8-ol (75 mg, 0.32 mmol) in anhydrous dioxane (1.1 mL). After stirring for 2 h at 80° C., the reaction mixture was cooled to room temperature, MeOH (5 mL) was added and the solvent was removed in vacuo. The residue was purified by flash chromatography on silica gel (elution with DCM/MeOH 20:1) to give the title compound. MS (m/z): 202.2 [M+H+].

後処理

  1. customto reach room temperature
  2. temperaturethe reaction mixture was cooled to room temperature
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by flash chromatography on silica gel (elution with DCM/MeOH 20:1)

出典と根拠

ORDレコード
ord-54d62f18e0aa4b46bf423f1b0d153528
出典データセット
uspto-grants-2013_04
特許番号
US08410134B2

反応ノート

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