Cesium carbonate → HCID 67072210, compound

HRID 1242334Notes

Reaction equation

HRID 1242334 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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.CN(C=O)C>[CH3:11][O:10][C:8]([C:5]1[CH:4]=[N:3][C:2]([C:17]2[CH:18]=[CH:19][C:14]([C:13]([F:24])([F:23])[F:12])=[CH:15][CH:16]=2)=[CH:7][N:6]=1)=[O:9]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 67072210HCID 67072210, compoundYield 27.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5.18 g (30 mmol) methyl 5-chloropyrazine-2-carboxylate in 150 ml degassed DMF was treated with 3.47 g (0.1 mmol) tetrakis(triphenylphosphine)palladium and heated at 80° C. 6.27 g (33 mmol) of 4-(trifluoromethyl)benzeneboronic acid and 14 66 g (45 mmol) of cesium carbonate were added and heated for 3.5 h. The reaction was cooled to RT and extracted with H2O (0° C.)/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (NaSO4) and evaporated. Purification by flash-chromatography on silica gel (heptane/AcOEt 95:5 to 2:1) gave 2.3 g (27%) of 5-(4-trifluoromethyl-phenyl)-pyrazine-2-carboxylic acid methyl ester.

Workup

  1. temperatureheated for 3.5 h
  2. temperatureThe reaction was cooled to RT
  3. extractionextracted with H2O (0° C.)/Et2O (3×)
  4. washThe organic phases were washed with aqueous 10% NaCl
  5. dry with materialdried (NaSO4)
  6. customevaporated
  7. customPurification by flash-chromatography on silica gel (heptane/AcOEt 95:5 to 2:1)

Sources & evidence

ORD record
ord-a06cc4ecdd3649feaa82f822c4061678
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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