Sodium Carbonate → HCID 86692493, compound

HRID 1748542Notes

Reaction equation

HRID 1748542 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[C:13]([Cl:19])=[N:14][CH:15]=[C:16](Br)[CH:17]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH:20]1(B(O)O)[CH2:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[C:13]([Cl:19])=[N:14][CH:15]=[C:16]([CH:20]3[CH2:22][CH2:21]3)[CH:17]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 2760897Cyclopropylboronic acidHCID 86692429HCID 86692429, compound

Product 1

HCID 86692493HCID 86692493, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 1-(5-bromo-2-chloropyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (2 g) in Reference Example 29 (1), cyclopropylboronic acid (724 mg), tetrakis(triphenylphosphine)palladium (0) (670 mg) and 2 M sodium carbonate aqueous solution (8.7 ml) was added tetrahydrofuran (12 ml), and stirred under reflux. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added to the reaction solution under ice-cooling, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate) to give 1-(2-chloro-5-cyclopropylpyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.13 g) as a white solid. MS (ESI) m/z: 306 (M+H)+.

Workup

  1. temperatureunder reflux
  2. customAfter completion of the reaction
  3. temperaturecooling
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4137f918b4cc4341a2448028129f2af5
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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