Sodium hydride → HCID 21949201, compound

HRID 2376881Notes

Reaction equation

HRID 2376881 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[CH:12]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:20]([NH:25][C:26](=O)[O:27]C1C=CC=CC=1)[CH2:21][CH2:22][CH2:23][CH3:24]>CN(C)C=O>[CH2:20]([NH:25][C:26]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[CH:12]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)=[O:27])[CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21949263HCID 21949263, compoundHCID 219493654-(1H-5-indolyloxy)-2-pyridinamine

Product 1

HCID 21949201HCID 21949201, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(1H-5-Indolyloxy)-2-pyridinamine (5.0 g, 22 mmol, CAS No. 417722-11-3) which was described in WO 02/32872 was dissolved in N,N-dimethylformamide (60 ml); sodium hydride (1.06 g, 27 mmol) was added thereto at room temperature; and the reaction mixture was stirred for 30 minutes. Phenyl N-n-pentylcarbamate (5.06 g, 24 mmol) while stirring at room temperature; and the reaction mixture was stirred for 30 minutes. The reaction mixture was partitioned between water and ethyl acetate (insoluble portions were perfectly dissolved by adding a small amount of methanol); and the organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH; hexane:ethyl acetate=1:1, ethyl acetate, ethyl acetate:methanol=95:5 in this order). The obtained crystals were suspended in hexane:ethanol=10:1, filtered off, washed with hexane, and dried under aeration to yield the title compound as colorless crystals (1.55 g, 4.58 mmol, 21%).

Workup

  1. customat room temperature
  2. stirringand the reaction mixture was stirred for 30 minutes
  3. customThe reaction mixture was partitioned between water and ethyl acetate (insoluble portions
  4. dissolutionwere perfectly dissolved
  5. additionby adding a small amount of methanol)
  6. washand the organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (Fuji Silysia NH
  10. filtrationethanol=10:1, filtered off
  11. washwashed with hexane
  12. customdried under aeration

Sources & evidence

ORD record
ord-13cafd24f9b44d43a325d8b580db4542
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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