HCID 118114032, compound → HCID 118114059, compound

HRID 706519Notes

Reaction equation

HRID 706519 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N+:32]([O-])=O)[C:5]([NH:8][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:21]=[N:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=3)=[C:14]([O:30][CH3:31])[CH:13]=2)[CH2:10][CH3:11])=[N:6][CH:7]=1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[I:1][C:2]1[CH:3]=[C:4]([NH2:32])[C:5]([NH:8][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:21]=[N:22][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:24][CH:25]=3)=[C:14]([O:30][CH3:31])[CH:13]=2)[CH2:10][CH3:11])=[N:6][CH:7]=1

Participants

5

Reactant 1

HCID 118114032HCID 118114032, compound

Product 1

HCID 118114059HCID 118114059, compoundYield 101.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
125 °C

Procedure

To a stirred suspension of 5-iodo-N-(1-(3-methoxy-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)phenyl)propyl)-3-nitropyridin-2-amine (1.25 g, 2.12 mmol) in acetic acid (20 mL) was added iron (0.714 g, 12.77 mmol). The yellow mixture was heated to 125° C. As the mixture was heated, the yellow color faded and a gray suspension formed. After 10 min, the mixture was allowed to cool to room temperature and was diluted with ethyl acetate (75 mL). The suspension was filtered through Celite with the aid of ethyl acetate (50 mL). The filtrate was washed with water (2×30 mL) and then with concentrated ammonium hydroxide (2×30 mL). The organic phase was dried over magnesium sulfate, filtered, and concentrated to provide 1.20 g (>100%) of 5-iodo-N2-(1-(3-methoxy-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)phenyl)propyl)pyridine-2,3-diamine as a brown oil.

Workup

  1. temperatureAs the mixture was heated
  2. customa gray suspension formed
  3. temperatureto cool to room temperature
  4. filtrationThe suspension was filtered through Celite with the aid of ethyl acetate (50 mL)
  5. washThe filtrate was washed with water (2×30 mL)
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a67636dc41514f1298490d61ccf06141
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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