Sodium Carbonate → HCID 68304375, compound

HRID 1842603Notes

Reaction equation

HRID 1842603 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[N:7][C:6]=12.[CH3:15][O:16][C:17]([C:19]1[S:20][C:21]([CH3:33])=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:23]=1)=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>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.O1CCOCC1>[CH3:15][O:16][C:17]([C:19]1[S:20][C:21]([CH3:33])=[C:22]([C:2]2[CH:3]=[N:4][N:5]3[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[N:7][C:6]=23)[CH:23]=1)=[O:18]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 46703107Methyl 5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylateHCID 68305187HCID 68305187, compound

Product 1

HCID 68304375HCID 68304375, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

3-Bromo-6-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (200 mg, 0.752 mmol), methyl-5-methyl-4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-thiophene-2-carboxylate (297 mg, 1.05 mmol), Pd(PPh3)4 (43.4 mg, 0.038 mmol), and 2 M sodium carbonate (aq) (750 μL, 1.50 mmol) were placed in a sealed tube. 1,4-dioxane (3.75 mL) was added and the reaction purged with N2 for 5 min. The reaction was heated to 85° C. for 7 h. After consumption of starting material, the reaction was cooled to room temperature, diluted with water and extracted 3× with ethyl acetate. The organic layers were combined, washed with brine, dried with sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (0-70% EtOAc/Hex) to afford the title compound (120 mg, 0.352 mmol). LRMS (APCI) calc'd for (C14H10F3N3O2S) [M+H]+, 342.0; found 342.0.

Workup

  1. customthe reaction purged with N2 for 5 min
  2. customAfter consumption of starting material
  3. temperaturethe reaction was cooled to room temperature
  4. additiondiluted with water
  5. extractionextracted 3× with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography (0-70% EtOAc/Hex)

Sources & evidence

ORD record
ord-886796b5e67f4f36afd798089c3a3c8f
Source dataset
uspto-grants-2015_02
Patent number
US08946237B2

Reaction notes

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