Methyl iodide → (3-(5-Chloro-2-cyano-4-fluorophenoxy)-3-(3-pyridinyl)propyl]carbamic acid 1,1 dimethylethyl ester

HRID 2179958Notes

Reaction equation

HRID 2179958 reaction equation
[H-].[Na+].[C:3]([OH:8])(=[O:7])C(O)=O.[NH2:9][CH2:10][CH2:11][CH:12]([O:19][C:20]1[CH:27]=[C:26]([Cl:28])[C:25]([F:29])=[CH:24][C:21]=1[C:22]#[N:23])[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.CI.[Cl-].[NH4+]>O1CCCC1>[CH3:12][C:13]([O:8][C:3](=[O:7])[NH:9][CH2:10][CH2:11][CH:12]([O:19][C:20]1[CH:27]=[C:26]([Cl:28])[C:25]([F:29])=[CH:24][C:21]=1[C:22]#[N:23])[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)([CH3:14])[CH3:18]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22489958HCID 22489958, compound

Product 1

HCID 86759694(3-(5-Chloro-2-cyano-4-fluorophenoxy)-3-(3-pyridinyl)propyl]carbamic acid 1,1 dimethylethyl esterYield 143.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (34.2 mg, 60% dispersion in oil, 0.86 mmol) was added to a solution of the product from Example 58 (c) (219 mg, 0.54 mmol) and methyl iodide (0.2 ml, 3.2 mmol) in tetrahydrofuran (4 ml) and stirred for 3 h. Aqueous ammonium chloride was added and the mixture was extracted with dichloromethane (three times). The combined organic extracts were dried (sodium sulphate), evaporated and purified by chromatography on silica eluting; with petrol—acetone to give the sub-title compound as a colourless oil (157 mg, 69%).

Workup

  1. extractionthe mixture was extracted with dichloromethane (three times)
  2. dry with materialThe combined organic extracts were dried (sodium sulphate)
  3. customevaporated
  4. custompurified by chromatography on silica eluting

Sources & evidence

ORD record
ord-87d828f4127d4b2aa4bfee92bc60c1b3
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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