Sodium hydride → HCID 21949351, compound

HRID 2376872Notes

Reaction equation

HRID 2376872 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+].[CH3:20][CH:21]([CH3:34])[CH2:22][CH2:23][NH:24][C:25](=O)[O:26]C1C=CC=CC=1>CN(C)C=O>[CH3:20][CH:21]([CH3:34])[CH2:22][CH2:23][NH:24][C:25]([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:26]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2802345HCID 2802345, compoundHCID 219493654-(1H-5-indolyloxy)-2-pyridinamine

Product 1

HCID 21949351HCID 21949351, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(1H-5-Indolyloxy)-2-pyridinamine (2.0 g, 8.9 mmol, CAS No. 417722-11-3) which was described in WO 02/32872 was dissolved in N,N-dimethylformamide (20 ml); and sodium hydride (426 mg, 10.7 mmol) was added thereto at room temperature while stirring. The reaction mixture was cooled with ice bath after 30 minutes; phenyl N-(3-methylbutyl)carbamate (2.02 g, 9.75 mmol) was added thereto; and the reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was partitioned between ethyl acetate and water; the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated; and the residue was purified by NH-silica gel column chromatography (hexane:ethyl acetate=3:1) to yield the title compound as crystals (1.45 g, 4.3 mmol, 48%).

Workup

  1. temperatureThe reaction mixture was cooled with ice bath after 30 minutes
  2. stirringand the reaction mixture was stirred for 3 hours at room temperature
  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 NH-silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-9a0ab2484f6d49be86d5c46f48c9bc00
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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