HCID 118324094, compound → HCID 118324107, compound

HRID 1778271Notes

Reaction equation

HRID 1778271 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:16][CH3:17])[CH:8]=[C:9]([C:12]([O:14]C)=O)[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([Mg]Br)=[CH:21][CH:20]=1>O1CCCC1>[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:16][CH3:17])[CH:8]=[C:9]([C:12]([C:22]3[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=3)([C:22]3[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=3)[OH:14])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 118324094HCID 118324094, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 118324107HCID 118324107, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 1000-mL 3-necked round-bottom flask, was placed methyl 4-bromo-8-methoxyquinoline-6-carboxylate (13 g, 43.90 mmol, 1.00 equip), tetrahydrofuran (500 mL), and (4-chlorophenyl)magnesium bromide (220 mL, 5.00 equip). The resulting solution was stirred for 3 hr at reflux temperature. The reaction was then quenched by the addition of water (400 mL). The resulting solution was extracted with ethyl acetate (3×300 mL) and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (2:1) to yield (4-bromo-8-methoxyquinolin-6-yl)bis(4-chlorophenyl)methanol as a yellow solid. LCMS (ES, m/z) 490 [M+H]+

Workup

  1. customInto a 1000-mL 3-necked round-bottom flask, was placed
  2. temperatureat reflux temperature
  3. customThe reaction was then quenched by the addition of water (400 mL)
  4. extractionThe resulting solution was extracted with ethyl acetate (3×300 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe solids were filtered out
  7. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-24fffceff8e847daa09e5313589fd00e
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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