Carbon Dioxide → HCID 11492556, compound

HRID 1009554Notes

Reaction equation

HRID 1009554 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]#[N:12])=[CH:8][CH:7]=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=2.CO[CH:18]1[CH2:22][CH2:21][CH:20](OC)O1.[C:25](=[O:28])(O)[O-].[Na+].C(=O)=O>C(O)(=O)C.O>[N+:13]([C:6]1[CH:5]=[C:4]2[C:9]([C:10]([C:11]#[N:12])=[C:2]([N:1]3[CH:18]=[CH:22][CH:21]=[CH:20]3)[NH:3]2)=[CH:8][CH:7]=1)([O-:15])=[O:14].[CH2:18]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([O:28][CH3:25])[CH:5]=2)[C:10]([C:11]#[N:12])=[CH:2]1)[CH3:22]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 790982,5-DimethoxytetrahydrofuranHCID 516892Sodium BicarbonateHCID 163613672-Amino-6-nitro-1H-indole-3-carbonitrile

Product 2

HCID 11492556HCID 11492556, compoundHCID 116441001-ethyl-6-methoxy-1H-indole-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2-amino-6-nitro-1H-indole-3-carbonitrile (362 mg, 1.79 mmol) in acetic acid (5 mL) is treated with 2,5-dimethoxytetrahydrofuran (0.30 mL, 2.27 mmol), and the solution is heated to reflux for 14 h. After cooling to ambient temperature, the solution is poured into water (100 mL), and solid sodium bicarbonate is added until CO2 evolution ceased. The mixture is extracted with EtOAc (2×100 mL), and the extracts are washed with saturated brine, combined, dried over MgSO4, filtered and concentrated. The residual material is separated by silica gel chromatography (EtOAc/hexanes, 1/4) to afford 6-nitro-2-pyrrol-1-yl-1H-indole-3-carbonitrile, compound 5, as a yellow solid (232 mg, 51%).

Workup

  1. temperaturethe solution is heated
  2. temperatureto reflux for 14 h
  3. extractionThe mixture is extracted with EtOAc (2×100 mL)
  4. washthe extracts are washed with saturated brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residual material is separated by silica gel chromatography (EtOAc/hexanes, 1/4)

Sources & evidence

ORD record
ord-a0b8e40e115d4ef080ffdfa67632ca14
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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