Allyl bromide → HCID 178456206, compound

HRID 1423361Notes

Reaction equation

HRID 1423361 reaction equation
[CH3:1][C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([OH:15])[C:5]=2[NH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:22](Br)[CH:23]=[CH2:24]>C1COCC1.CN1C(=O)CCC1>[CH2:24]([N:4]1[C:5]2[C:6]([OH:15])=[N:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]=2[C:2]([CH3:1])=[CH:3]1)[CH:23]=[CH2:22]

Participants

6

Reactant 3

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

Product 1

HCID 178456206HCID 178456206, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 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-c405bfabf2424e459828da0a6946a40e
Source dataset
uspto-grants-2015_01
Patent number
US08927569B2

Reaction notes

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