Sodium hydride → HCID 66764424, compound

HRID 2207342Notes

Reaction equation

HRID 2207342 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]1.[Br:15][C:16]1[CH:17]=[CH:18][C:19](F)=[N:20][CH:21]=1>CN(C=O)C.C([O-])(O)=O.[Na+]>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([O:3][CH:4]2[CH2:5][CH2:6][CH:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:8][CH2:9]2)=[N:20][CH:21]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 86973Ethyl 4-hydroxycyclohexanecarboxylateHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 66764424HCID 66764424, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

NaH (0.250 g, 6.25 mmol) was added to a mixture of ethyl 4-hydroxycyclohexanoate (0.916 ml, 5.68 mmol), and 5-bromo-2-fluoropyridine (0.585 mL, 5.68 mmol) in DMF (15 mL) at room temperature under an Argon atmosphere. The reaction mixture was heated to 80° C. for 2.5 hours. Upon cooling, the reaction mixture was diluted with saturated NaHCO3 (50 mL), and extracted with ethyl acetate (50 mL) and diethyl ether (50 mL). The organic layer was washed with water, brine, dried over sodium sulfate, filtered, concentrated in vacuo and purified by silica gel chromatography (hexanes/ethyl Acetate) to afford ethyl 4-[(5-bromopyridin-2-yl)oxy]cyclohexanecarboxylate. MS ESI calc'd. for C14H19BrNO3 [M+H]+ 328 and 330. found 328 and 330.

Workup

  1. temperatureUpon cooling
  2. extractionextracted with ethyl acetate (50 mL) and diethyl ether (50 mL)
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography (hexanes/ethyl Acetate)

Sources & evidence

ORD record
ord-9cda6d7a6f1d45e5b5dcff8eb34a387e
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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