(6-Bromo-naphthalen-2-yl)-(6,7-dimethoxy-quinolin-4-yl)-methanol → HCID 67520211, compound

HRID 1925263Notes

Reaction equation

HRID 1925263 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]([C:14]1[C:23]3[C:18](=[CH:19][C:20]([O:26][CH3:27])=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][CH:15]=1)O)[CH:6]=[CH:5]2>C(O)=O.[Zn]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][C:14]1[C:23]3[C:18](=[CH:19][C:20]([O:26][CH3:27])=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][CH:15]=1)[CH:6]=[CH:5]2

Participants

4

Reactant 1

HCID 67520432(6-Bromo-naphthalen-2-yl)-(6,7-dimethoxy-quinolin-4-yl)-methanol

Product 1

HCID 67520211HCID 67520211, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 284Formic AcidSolvent

Procedure

To a solution of (6-bromo-naphthalen-2-yl)-(6,7-dimethoxy-quinolin-4-yl)-methanol (Step e, 0.55 g, 1.3 mmol) in formic acid (10 mL), was added Zn dust (500 mg, 7.6 mmol). The suspension was heated at reflux for 6 h and the solvent was removed in vacuo. The resulting residue was worked up with 1N NaOH and extracted with CH2Cl2 3×. The combined organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified with silica gel column chromatography (40-65% EtOAc/Hexane) to give the titled compound. MS (ESI, pos. ion) m/z: 408.1 (M+1).

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 6 h
  3. customthe solvent was removed in vacuo
  4. extractionextracted with CH2Cl2 3×
  5. washThe combined organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude was purified with silica gel column chromatography (40-65% EtOAc/Hexane)

Sources & evidence

ORD record
ord-fc9d2cf8074146c0b197022be95e911a
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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