Allyl bromide → 3-Allyl-1-methyl-3H-pyrrolo[2,3-e]quinolin-4-ol

HRID 2045722Notes

Reaction equation

HRID 2045722 reaction equation
C[C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6](O)[C:5]=2[NH:4][CH:3]=1.[C:16]([O-:19])([O-])=O.[Cs+].[Cs+].[CH2:22](Br)[CH:23]=C.[CH2:26]1COCC1>CN1C(=O)CCC1>[CH2:10]([CH:9]1[CH:16]([OH:19])[C:5]23[N:4]=[CH:3][CH:2]=[C:14]2[CH:13]=[CH:12][CH:11]=[C:6]3[N:7]([CH3:26])[CH2:8]1)[CH:22]=[CH2:23]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 178430818HCID 178430818, compound

Product 1

HCID 668963203-Allyl-1-methyl-3H-pyrrolo[2,3-e]quinolin-4-olYield 54%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 1-methyl-3H-pyrrolo[2,3-c]quinolin-4-ol (1.2 g, 6.05 mmol) in a mixture of THF (30 mL) and NMP (60 mL) was treated with Cs2CO3 (2.95 g, 9.08 mmol). Allyl bromide (0.524 mL, 6.06 mmol) was added dropwise, and the resulting mixture was stirred at 40° C. for 12 h. The mixture was cooled and quenched with aqueous HCl (1 N) and EtOAc. The organic layer was separated, washed with aqueous HCl (1 N), brine, and dried over Na2SO4. Filtration and removal of the volatiles gave a residue that was triturated with Et2O to give the title compound (0.78 g, 54%) as a solid. LCMS (ES+) m/z 239 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. customquenched with aqueous HCl (1 N) and EtOAc
  3. customThe organic layer was separated
  4. washwashed with aqueous HCl (1 N), brine
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration and removal of the volatiles
  7. customgave a residue that
  8. customwas triturated with Et2O

Sources & evidence

ORD record
ord-76fdf8fec2e44cdab698ca6c227d6329
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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