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

HRID 1959568Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 80 °C

Procedure

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+].

Workup

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

Sources & evidence

ORD record: ord-54d62f18e0aa4b46bf423f1b0d153528
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410134B2

Reaction notes

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