Water → HCID 131736022, compound

HRID 1049533Notes

Reaction equation

HRID 1049533 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[F:17][CH:18]([C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:35]=2[F:42])=[C:30]([CH2:43][C:44]([CH3:47])([CH3:46])[CH3:45])[N:29]=1)[CH2:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=O.O>C1COCC1>[F:17][CH:18]([C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:35]=2[F:42])=[C:30]([CH2:43][C:44]([CH3:47])([CH3:46])[CH3:45])[N:29]=1)[CH2:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 117759731HCID 117759731, compound

Product 1

HCID 131736022HCID 131736022, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, to a suspension of 60% sodium hydride (21 mg) in THF (2.0 mL) was added ethyl diethylphosphonoacetate (117 μL) at 0° C., and the mixture was stirred at room temperature for 5 min. To the obtained colorless solution was added 3-(2-fluoro-2-(5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)ethyl)benzaldehyde (entire amount) obtained in Example 36, step 0, at 0° C. and the mixture was stirred at room temperature for 20 min. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (119 mg) as a colorless oil.

Workup

  1. customobtained in Example 36, step 0, at 0° C.
  2. stirringthe mixture was stirred at room temperature for 20 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c67ce5825a334003b0c7fb4a2e69fb44
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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