Sodium hydride → HCID 86759694, compound

HRID 2179957Notes

Reaction equation

HRID 2179957 reaction equation
[H-].[Na+].[OH:3][CH:4]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[Cl:21][C:22]1[C:29]([F:30])=[CH:28][C:25]([C:26]#[N:27])=[C:24](F)[CH:23]=1>O1CCCC1>[Cl:21][C:22]1[C:29]([F:30])=[CH:28][C:25]([C:26]#[N:27])=[C:24]([CH:23]=1)[O:3][CH:4]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 112753024-Chloro-2,5-difluorobenzonitrileHCID 69799429[3-Hydroxy-3-(3-pyridinyl)propyl]carbamic acid 1,1-dimethylethyl ester

Product 1

HCID 86759694HCID 86759694, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (141 mg, 60% dispersion in oil) was added to a solution of the product from step (b) (785 mg, 2.96 mmol) and 4-chloro-2,5-difluorobenzonitrile (546 mg, 3.75 mmol) in tetrahydrofuran (9 ml) and the resultant suspension was stirred for 0.5 h. The mixture was quenched with saturated aqueous ammonium chloride, basified to pH 8 and extracted with ethyl acetate (three times). The combined organic extracts were dried (sodium sulphate), evaporated and purified by chromatography on silica eluting with petrol—acetone to give 1.05 g (88%) of the sub-title compound as a colourless oil.

Workup

  1. customThe mixture was quenched with saturated aqueous ammonium chloride
  2. extractionextracted with ethyl acetate (three times)
  3. dry with materialThe combined organic extracts were dried (sodium sulphate)
  4. customevaporated
  5. custompurified by chromatography on silica eluting with petrol—acetone

Sources & evidence

ORD record
ord-e90cccf4c60846e3b9d4703c2fbf62f6
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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