Bromide ion → HCID 24989976, compound

HRID 222126Notes

Reaction equation

HRID 222126 reaction equation
C([N+:8]1[CH:17]=[CH:16][C:15]2[C:14]3[N:18]([CH3:31])[C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])=[C:20]([C:21](=[O:23])[NH2:22])[C:13]=3[CH2:12][CH2:11][C:10]=2[CH:9]=1)C1C=CC=CC=1.[Br-].CC(C)([O-])C.[K+]>CS(C)=O.C1COCC1>[CH3:31][N:18]1[C:14]2[C:15]3[CH:16]=[CH:17][N:8]=[CH:9][C:10]=3[CH2:11][CH2:12][C:13]=2[C:20]([C:21]([NH2:22])=[O:23])=[C:19]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30]

Participants

6

Reactant 3

HCID 259Bromide ionHCID 23665647Potassium tert-butoxideHCID 68707582HCID 68707582, compound

Product 1

HCID 24989976HCID 24989976, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-benzyl-3-carbamoyl-1-methyl-2-o-tolyl-4,5-dihydro-1H-pyrrolo[2,3-f]isoquinolin-7-ium; bromide XXV (1.64 mmol) in dry DMSO (1 mL), 1M potassium tert-butoxide (11.5 mmol) in THF was added. The solution was bubbled with dry air overnight. Volatiles were removed, the residue was suspended in DCM, washed with water, dried (Na2SO4), filtered and the solvent evaporated. Chromatography on silica gel (eluant: DCM/MeOH 20:1) afforded the desired compound.

Workup

  1. customThe solution was bubbled
  2. customwith dry air overnight
  3. customVolatiles were removed
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-67884f1b8cc24f4a8a8dc6f7326d0e7a
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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