Carbon Dioxide → HCID 11492556, compound

HRID 907124Notes

Reaction equation

HRID 907124 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) was treated with 2,5-dimethoxytetrahydrofuran (0.30 mL, 2.27 mmol), and the solution was heated to reflux for 14 h. After cooling to ambient temperature, the solution was poured into water (100 mL), and solid sodium bicarbonate was added until CO2 evolution ceased. The mixture was extracted with EtOAc (2×100 mL), and the extracts were washed with saturated brine, combined, dried over MgSO4, filtered and concentrated. The residual material was 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 was heated
  2. temperatureto reflux for 14 h
  3. extractionThe mixture was extracted with EtOAc (2×100 mL)
  4. washthe extracts were washed with saturated brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residual material was separated by silica gel chromatography (EtOAc/hexanes, 1/4)

Sources & evidence

ORD record
ord-88c94c076d1547f698634e383071db4a
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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