Sodium hydride → HCID 21949246, compound

HRID 2376877Notes

Reaction equation

HRID 2376877 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]([CH:22]([NH:25][C:26](=O)[O:27]C1C=CC=CC=1)[CH2:23][CH3:24])[CH3:21]>CN(C)C=O>[CH2:20]([CH:22]([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])[CH2:23][CH3:24])[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21949154HCID 21949154, compoundHCID 219493654-(1H-5-indolyloxy)-2-pyridinamine

Product 1

HCID 21949246HCID 21949246, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(1H-5-Indolyloxy)-2-pyridinamine (1.85 g, 8.2 mmol, CAS No. 417722-11-3) which was described in WO 02/32872 was dissolved in N,N-dimethylformamide (20 ml); and sodium hydride (394 mg, 9.84 mmol) was added thereto while stirring at room temperature. The reaction mixture was cooled with ice bath after 30 minutes; phenyl N-(1-ethylpropyl)carbamate (1.87 g, 9.03 mmol); and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was partitioned between ethyl acetate and water; the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, concentrated; and the residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane:ethyl acetate=3:1) to yield the title compound as crystals (1.95 g, 5.8 mmol, 71%).

Workup

  1. temperatureThe reaction mixture was cooled with ice bath after 30 minutes
  2. stirringand the reaction mixture was stirred at room temperature for 3 hours
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customand the residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-e1130d30f09843a3bd97c3723bab99be
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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