Sodium Bicarbonate → 9-bromo-2-carboxymethyloxy-5-(3-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-one

HRID 850781Notes

Reaction equation

HRID 850781 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:24](=[O:34])[C:25]([CH2:27][C:28]5[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=5)=[CH:26][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])[CH:10]=3.C(=O)([O-])O.[Na+]>C(O)(=O)C.Br>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:24](=[O:34])[C:25]([CH2:27][C:28]5[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=5)=[CH:26][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH2:16][C:17]([OH:19])=[O:18])[CH:10]=3

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 193648749-bromo-2-t-butoxycarbonylmethyloxy-5-(3-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-one

Product 1

HCID 193648899-bromo-2-carboxymethyloxy-5-(3-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-oneYield 79%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

9-bromo-2-t-butoxycarbonylmethyloxy-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (57 mg) produced in Example 103 was dissolved in acetic acid (0.5 ml) and 48% HBr (0.5 ml), and the solution was stirred at 60° C. for 1 hour and allowed to cool. Saturated aqueous solution of sodium hydrogencarbonate was added to pH 7, and the crystals precipitated were recovered by filtration, washed with water, ethanol and ether in succession, and recovered by filtration to obtain the title compound (40 mg, 79%).

Workup

  1. temperatureto cool
  2. customthe crystals precipitated
  3. filtrationwere recovered by filtration
  4. washwashed with water, ethanol and ether in succession
  5. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-0f53ada84bb142cdb975e08f7f427070
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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