6-Bromoquinoline → HCID 67223792, compound

HRID 500131Notes

Reaction equation

HRID 500131 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.C[S-:13].[Na+].Br[CH2:16][CH:17]([O:20][CH3:21])[O:18][CH3:19]>CN(C)C(=O)C.C(O)C>[CH3:19][O:18][CH:17]([O:20][CH3:21])[CH2:16][S:13][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 792436-BromoquinolineHCID 816722-Bromo-1,1-dimethoxyethaneHCID 4378561Sodium methanethiolate

Product 1

HCID 67223792HCID 67223792, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 6-bromoquinoline (0.832 g, 4.0 mmol) in N,N-dimethylacetamide (4.0 mL) was added sodium methyl mercaptide (0.841 g, 12.0 mmol). The reaction mixture was heated at 150° C. for 2 h. After cooling, 2-bromo-1,1-dimethoxyethane (1.41 mL, 12.0 mol) was then added, and the reaction mixture was diluted with ethanol (5 mL), and heated at 80° C. for 1 h. After the precipitated salt was isolated by filtration, the mother liquor was evaporated under reduced pressure. The residue was diluted with diethyl ether (50 mL), washed with water, brine, dried over sodium sulfate, filtered, and concentrated. The residue was directly used in the next reaction step without further purification. LCMS: (M+H)=249.9.

Workup

  1. temperatureAfter cooling
  2. temperatureheated at 80° C. for 1 h
  3. customAfter the precipitated salt was isolated by filtration
  4. customthe mother liquor was evaporated under reduced pressure
  5. additionThe residue was diluted with diethyl ether (50 mL)
  6. washwashed with water, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was directly used in the next reaction step without further purification

Sources & evidence

ORD record
ord-655e87f21cc745dd850d0af1d3d939cf
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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