Ethanol → HCID 117988061, compound

HRID 2206235Notes

Reaction equation

HRID 2206235 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([O:11][CH3:12])[C:3]=1[N:13]1[C:21]2[CH:20]=[CH:19][NH:18][C:17](=[O:22])[C:16]=2[C:15]([C:23]2[CH:24]=[C:25]([C:28]([NH2:30])=[O:29])[S:26][CH:27]=2)=[CH:14]1.[Cl-].[Ca+2].[Cl-].C(O)C>O>[NH2:8][C:6]1[CH:5]=[C:4]([O:11][CH3:12])[C:3]([N:13]2[C:21]3[CH:20]=[CH:19][NH:18][C:17](=[O:22])[C:16]=3[C:15]([C:23]3[CH:24]=[C:25]([C:28]([NH2:30])=[O:29])[S:26][CH:27]=3)=[CH:14]2)=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 5284359Calcium ChlorideHCID 117987853HCID 117987853, compound

Product 1

HCID 117988061HCID 117988061, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(1-(2-fluoro-6-methoxy-4-nitrophenyl)-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-3-yl)thiophene-2-carboxamide (45.0 mg) and calcium chloride (11.7 mg) in a mixed solvent of ethanol (5 ml) and water (1 ml) was added reduced iron (29.3 mg), and the mixture was stirred at 100° C. for 2 hr. The insoluble substance was removed by the filtration, and washed with water and ethyl acetate. The filtrate was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (30.0 mg).

Workup

  1. customThe insoluble substance was removed by the filtration
  2. washwashed with water and ethyl acetate
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-30f827a07a2a4b8b912043024005b289
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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