Sodium hydride → HCID 66707388, compound

HRID 2114685Notes

Reaction equation

HRID 2114685 reaction equation
[CH2:1]([C:3]1[NH:7][N:6]=[C:5]([CH:8]([OH:10])[CH3:9])[C:4]=1[O:11][C:12]1[CH:13]=[C:14]([C:20]#[N:21])[CH:15]=[C:16]([CH:19]=1)[C:17]#[N:18])[CH3:2].Br[CH2:23][CH2:24][O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27]1.[H-].[Na+]>CN(C)C=O>[CH2:1]([C:3]1[N:7]([CH2:23][CH2:24][O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[N:6]=[C:5]([CH:8]([OH:10])[CH3:9])[C:4]=1[O:11][C:12]1[CH:19]=[C:16]([C:17]#[N:18])[CH:15]=[C:14]([CH:13]=1)[C:20]#[N:21])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 21949809HCID 21949809, compound

Product 1

HCID 66707388HCID 66707388, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of the pyrazole from Example 263 (197 mg, 0.70 mmol) in dimethylformamide (3 ml) at 0° C. was added 2-(2-bromoethoxy)tetrahydro-2H-pyran (105 μl, 0.70 mmol) followed by sodium hydride (31 mg, 0.77 mmol). After 15 minutes the cooling bath was removed and the mixture was stirred at room temperature for 60 hours. The reaction mixture was quenched by addition of saturated aqueous ammonium chloride solution (0.5 ml) and then concentrated under reduced pressure. The crude product mixture was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (a gradient from 100:0 to 95:5, by volume) to provide the title compound (84 mg) as a white foam which reverts to an oil on standing.

Workup

  1. customAfter 15 minutes the cooling bath was removed
  2. customThe reaction mixture was quenched by addition of saturated aqueous ammonium chloride solution (0.5 ml)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product mixture was purified by flash chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-4fe3d86a44ab4ac8beb1b7d802d585aa
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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