Sulfuric Acid → 4-(2-Amino)ethyloxy-9-benzyl-2-methoxycarbazole-5-carboxamide

HRID 51341

Reaction equation

HRID 51341 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.OS(O)(=O)=O.[CH2:17]([N:24]1[C:36]2[CH:35]=[C:34]([O:37][CH3:38])[CH:33]=[C:32]([O:39][CH2:40][C:41]#[N:42])[C:31]=2[C:30]2[C:29]([C:43]([NH2:45])=[O:44])=[CH:28][CH:27]=[CH:26][C:25]1=2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[NH2:42][CH2:41][CH2:40][O:39][C:32]1[C:31]2[C:30]3[C:29]([C:43]([NH2:45])=[O:44])=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]([CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:36]=2[CH:35]=[C:34]([O:37][CH3:38])[CH:33]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 101569139-Benzyl-4-cyanomethyloxy-2-methoxycarbazole-5-carboxamideHCID 68718528lithium aluminium hydride THF

Product 1

HCID 227398894-(2-Amino)ethyloxy-9-benzyl-2-methoxycarbazole-5-carboxamideYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1.25 ml (1.25 mmol) 1M lithium aluminum hydride/THF in 8.3 ml THF at 0° C. was added H2SO4(34.5 μl, 0.63 mmol) dropwise over 5 min. The mixture was allowed to stir at room temperature 1 hour, then a suspension of 9-benzyl-4-cyanomethyloxy-2-methoxycarbazole-5-carboxamide (0.32 g, 0.83 mmol) in 8.3 ml THF was added dropwise at a rate which kept the temperature below 26° C. After an additional 45 minutes, the reaction was quenched with 0.32 ml 1:1 THF/H2O, 0.48 ml 13% NaOH, and finally 51 μl H2O. The reaction was diluted with EtOAc and saturated NaHCO3, and the layers separated. The organic layer was extracted with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 9:1:0.1 CH2Cl2/MeOH/NH4OH to give the subtitled product (148 mg, 46%). MS (ES+) 390

Workup

  1. additionwas added dropwise at a rate which
  2. customthe temperature below 26° C
  3. waitAfter an additional 45 minutes
  4. customthe reaction was quenched with 0.32 ml 1:1 THF/H2O, 0.48 ml 13% NaOH, and finally 51 μl H2O
  5. additionThe reaction was diluted with EtOAc and saturated NaHCO3
  6. customthe layers separated
  7. extractionThe organic layer was extracted with brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated in vacuo
  10. customThe residue was chromatographed on silica gel eluting with 9:1:0.1 CH2Cl2/MeOH/NH4OH

Sources & evidence

ORD record
ord-fa967103d34b4338a056995235c4af0d
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Linked notes

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