Bicarbonate Ion → HCID 11587886, compound

HRID 2067941Notes

Reaction equation

HRID 2067941 reaction equation
CC([O-])(C)C.[K+].O.Cl[C:9]([C:20]1[C:24]([CH3:25])=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[N:22]([CH3:33])[N:21]=1)=[C:10]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=1)C=O.C(=O)(O)[O-]>C1COCC1>[Cl:19][C:15]1[CH:14]=[C:13]([C:10]#[C:9][C:20]2[C:24]([CH3:25])=[C:23]([C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[N:22]([CH3:33])[N:21]=2)[CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86602965HCID 86602965, compound

Product 1

HCID 11587886HCID 11587886, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

To 11 ml of THF cooled to 0° C. were added 0.26 g of Potassium tert-butylate and 20 μl of water. Then a solution of 0.40 g 3-Chloro-2-(2-chloro-pyridin-4-yl)-3-[5-(4-fluoro-phenyl)-1,4-dimethyl-1H-pyrazol-3-yl]-propenal in 7 ml of THF was added at 0°. After stirring for 1 h at 5° C., 10 ml of 5% Bicarbonate solution were added and the aqueous phase was extracted twice with Ethyl acetate. The combined organic phases were washed with water and brine, dried over magnesium sulfate, filtered and evaporated. The crude product (0.28 g, yellow oil) was purified by chromatography on silica gel (Heptane/Ethyl acetate 4:1). The desired product was obtained as a white solid (0.275 g, 82%), MS: m/e=326.0 (M+).

Workup

  1. extractionthe aqueous phase was extracted twice with Ethyl acetate
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product (0.28 g, yellow oil) was purified by chromatography on silica gel (Heptane/Ethyl acetate 4:1)

Sources & evidence

ORD record
ord-bf745c8c437c412ca3377726204fb88f
Source dataset
uspto-grants-2012_10
Patent number
US08293916B2

Reaction notes

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