Chloroform → HCID 86692503, compound

HRID 1748554Notes

Reaction equation

HRID 1748554 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[C:17]([CH3:18])=[CH:16][C:15](Cl)=[CH:14][N:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH:20]1(B(O)O)[CH2:22][CH2:21]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(Cl)(Cl)Cl>O1CCOCC1.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH:20]3[CH2:22][CH2:21]3)=[CH:14][N:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 6212ChloroformHCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 86692502HCID 86692502, compound

Product 1

HCID 86692503HCID 86692503, compoundYield 75.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 12976736Bis(ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane);iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 1-(5-chloro-3-methylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (600 mg), cyclopropylboronic acid (369 mg), 1,1′-bis(di-tert-butylphosphino)ferrocene (51 mg), palladium acetate (24 mg) and tripotassium phosphate (1.83 g) in 1,4-dioxane (5 ml) was stirred under reflux for 6 hours. After completion of the reaction, the mixture was allowed to cool, and chloroform was added, filtered through Celite, and then the filtrate was evaporated in vacuo. The obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate) to give 1-(5-cyclopropyl-3-methylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (462 mg) as a yellow solid. MS (ESI) m/z: 286 (M+H)+.

Workup

  1. temperatureunder reflux for 6 hours
  2. customAfter completion of the reaction
  3. temperatureto cool
  4. filtrationfiltered through Celite
  5. customthe filtrate was evaporated in vacuo
  6. customThe obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b32ffbe27637406aa7cc861e9d9dec5e
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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