Sodium Carbonate → HCID 86692428, compound

HRID 1748459Notes

Reaction equation

HRID 1748459 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](B1OC(C)(C)C(C)(C)O1)=[CH2:21].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.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]=[CH2:21])[CH:17]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86692429HCID 86692429, compound

Product 1

HCID 86692428HCID 86692428, compoundYield 72.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Tetrahydrofuran (75 ml) was added to 1-(5-bromo-2-chloropyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (3 g) described in Reference Example 29, vinylboronic acid pinacol ester (2.01 g), tetrakis(triphenylphosphine)palladium (504 mg) and 2M aqueous solution of sodium carbonate (15.2 ml) and stirred at 90° C. for 4 hours. The reaction solution was cooled to 0° C., and a saturated aqueous solution of ammonium chloride and ethyl acetate were added therein. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified with column chromatography (n-hexane/ethyl acetate) to give 1-(2-chloro-5-vinylpyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.84 g).

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified with column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e2d0d34f92ed4c9e9bc88a7f5757dcd3
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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