Sodium Carbonate → HCID 71093733, compound

HRID 1424534

Reaction equation

HRID 1424534 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9](Cl)[O:8][N:7]=1)=[O:5])[CH3:2].[C:12]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[C:16]([F:23])[CH:15]=1)#[N:13].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:17]2[CH:18]=[CH:19][C:14]([C:12]#[N:13])=[CH:15][C:16]=2[F:23])[O:8][N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 447552094-Cyano-2-Fluorophenylboronic AcidHCID 66831968Ethyl 5-chloro-1,2-oxazole-3-carboxylate

Product 1

HCID 71093733HCID 71093733, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-chloro-isoxazole-3-carboxylic acid ethyl ester (600 mg), 4-cyano-2-fluorophenylboronic acid (665 mg), and aqueous Na2CO3 solution (2 M; 4.41 mL) in 1,4-dioxane (15 mL) is purged with argon for 15 min prior to the addition of Pd(PPh3)4 (276 mg). The reaction mixture is heated under an argon atmosphere to 140° C. for 20 min in a microwave oven. The solvent is evaporated in vacuo and the residue is mixed with water and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified by silica gel chromatography (cyclohexane/ethyl acetate 80:20→50:50). LC (method 3): tR=1.50 min; Mass spectrum (ESI+): m/z=261 [M+H]+.

Workup

  1. customis purged with argon for 15 min
  2. additionto the addition of Pd(PPh3)4 (276 mg)
  3. customThe solvent is evaporated in vacuo
  4. additionthe residue is mixed with water and ethyl acetate
  5. extractionThe aqueous phase is extracted with ethyl acetate
  6. washthe combined extracts are washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe crude product is purified by silica gel chromatography (cyclohexane/ethyl acetate 80:20→50:50)

Sources & evidence

ORD record
ord-ebda754e58264352ba8eb380841b441d
Source dataset
uspto-grants-2015_01
Patent number
US08927726B2

Linked notes

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