5-(2-Aminopyridin-4-yloxy)-2,3-dihydro-1H-indole-1-carboxylic acid methylamide → N1-Methyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamide

HRID 2215499Notes

Reaction equation

HRID 2215499 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=3)=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)=[O:4]>C(O)(=O)C.C([O-])(=O)C.[Mn+3].C([O-])(=O)C.C([O-])(=O)C>[CH3:1][NH:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)=[O:4]

Participants

4

Reactant 1

HCID 210548125-(2-Aminopyridin-4-yloxy)-2,3-dihydro-1H-indole-1-carboxylic acid methylamide

Product 1

HCID 21949141N1-Methyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamideYield 61%

Reagents, catalysts & solvents 2

HCID 160554manganese(III) acetate dihydrateCatalyst2×HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

5-(2-Aminopyridin-4-yloxy)-2,3-dihydro-1H-indole-1-carboxylic acid methylamide (40 mg, 0.14 mmol) was dissolved in acetic acid (0.9 ml), manganese (III) acetate (29 mg, 0.17 mmol) was added thereto and the reaction mixture was stirred at 70° C. for 3.5 hours. Manganese (III) acetate (29 mg, 0.17 mmol) was further added, and the reaction mixture was further stirred at 70° C. for 0.5 hours. After naturally cooled to room temperature, the reaction mixture was partitioned between ethyl acetate and saturated aqueous solution of sodium hydrogencarbonate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were suspended in diethyl ether:acetone=3:1, filtered off, washed with diethyl ether, and dried under aeration to yield the title compound (24 mg, 0.085 mmol, 61%) as colorless crystals.

Workup

  1. stirringthe reaction mixture was further stirred at 70° C. for 0.5 hours
  2. temperatureAfter naturally cooled to room temperature
  3. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous solution of sodium hydrogencarbonate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationacetone=3:1, filtered off
  8. washwashed with diethyl ether
  9. customdried under aeration

Sources & evidence

ORD record
ord-4b07983ee1fd4bac98c9723558b3773a
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

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