Diethyl Ether → HCID 21078399, compound

HRID 1374897Notes

Reaction equation

HRID 1374897 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1.Br[C:13](Br)([CH2:24][CH3:25])[C:14]([NH:16][C:17]([CH3:23])([CH3:22])[C:18]#[C:19][CH2:20][CH3:21])=[O:15].C(=O)([O-])[O-].[K+].[K+].C(OCC)C>CN(C)C=O.O>[CH3:11][O:10][C:8]([C:6]1[CH:7]=[C:2]([O:1][CH:13]([CH2:24][CH3:25])[C:14]([NH:16][C:17]([CH3:23])([CH3:22])[C:18]#[C:19][CH2:20][CH3:21])=[O:15])[CH:3]=[N:4][CH:5]=1)=[O:9]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 354317Methyl 5-hydroxypyridine-3-carboxylateHCID 21078402HCID 21078402, compound

Product 1

HCID 21078399HCID 21078399, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3-Hydroxy-5-methoxycarbonylpyridine (1.68 g, prepared using the method described in Bull. Acad. Sci. (Chem. Div.), (1976), 598) and 2-bromobromo-N-(5-methylhex-3-yn-5-yl)-butyramide (3.06 g) were dissolved in dry N,N-dimethylformamide (30 ml) containing anhydrous potassium carbonate (2.35 g). The mixture was heated to 70° C. for 3 hours with stirring, cooled to ambient temperature, diluted with water and extracted with diethyl ether (three times). The organic extracts were combined, washed with water (three times), dried over magnesium sulphate and evaporated under reduced pressure to give a brown gum. The gum was fractionated by chromatography (silica; diethyl ether) to give the required product, 2.38 g, as a yellow oil.

Workup

  1. temperaturecooled to ambient temperature
  2. extractionextracted with diethyl ether (three times)
  3. washwashed with water (three times)
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure
  6. customto give a brown gum

Sources & evidence

ORD record
ord-dc898de558ae462384208164512c2e56
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

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