3,4-dihydro-2H-pyran → 5-Bromo-8-[(tetrahydro-2H-pyran-2-yloxy)methyl]quinoline

HRID 1849998Notes

Reaction equation

HRID 1849998 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1>C(Cl)Cl.O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][O:13][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][O:14]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

6

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 72183353(5-Bromoquinolin-8-yl)methanol

Product 1

HCID 867151505-Bromo-8-[(tetrahydro-2H-pyran-2-yloxy)methyl]quinolineYield 128.4%

Reagents, catalysts & solvents 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromoquinolin-8-yl)methanol (8.0 g, 33.6 mmol) in methylene chloride (120 mL) were added pyridinium p-toluenesulfonate (844 mg, 3.3 mmol) and 3,4-dihydro-2H-pyran (6.1 mL, 67.2 mmol) and stirred at RT for 16 h. The reaction mixture was diluted with water, extracted with methylene chloride, dried with magnesium sulfate and concentrated. Purification by MPLC (20% ethyl acetate in hexanes) afforded 13.9 g of the title compound as a colorless oil.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated
  4. customPurification by MPLC (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-eaac7f16032f41b59464a92439ee963d
Source dataset
uspto-grants-2015_02
Patent number
US08957051B2

Reaction notes

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