Bromide ion → HCID 68707595, compound

HRID 222125Notes

Reaction equation

HRID 222125 reaction equation
C([N+:8]1[CH:17]=[CH:16][C:15]2[C:14]3[N:18]([CH3:33])[C:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[CH3:32])=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O: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>[CH2:24]([O:23][C:21]([C:20]1[C:13]2[CH2:12][CH2:11][C:10]3[CH:9]=[N:8][CH:17]=[CH:16][C:15]=3[C:14]=2[N:18]([CH3:33])[C:19]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:32])=[O:22])[CH3:25]

Participants

6

Reactant 3

HCID 259Bromide ionHCID 23665647Potassium tert-butoxideHCID 68704757HCID 68704757, compound

Product 1

HCID 68707595HCID 68707595, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-benzyl-3-ethoxycarbonyl-1-methyl-2-o-tolyl-4,5-dihydro-1H-pyrrolo[2,3-f]isoquinolin-7-ium; bromide XXIIIA (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 title compound. ESI (+) MS: m/z 347 (MH+). 1H NMR: 1.1 (t, J=7.1, 3H), 2.15 (s, 3H), 2.9 (m, 2H), 3.02 (m, 2H), 4.05 (q, J=7.1, 2H), 4.2 (s, 3H), 7.2-7.4 (m, 4H), 7.48 (d, J=5.1, 1H), 8.36 (d, J=5.1, 1H), 8.4 (s, 1H).

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-52ad220578d6468fa7571d09f9c501a0
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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