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

HRID 1959568노트

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HRID 1959568 반응식
[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]

참가 물질

8

반응물 3

HCID 887MethanolHCID 670771594-Bromo-2-methyl-quinolin-8-olHCID 178506895HCID 178506895, 화합물

생성물 1

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

시약·촉매·용매 4

HCID 3007855Zincchloride촉매HCID 11071931Dichloropalladium--(ethane-1,2-diyl)bis(diphenylphosphane) (1/1)촉매HCID 8028Tetrahydrofuran용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

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+].

후처리

  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)

출처 및 근거

ORD 기록
ord-54d62f18e0aa4b46bf423f1b0d153528
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410134B2

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