Potassium Carbonate → HCID 69362609, compound

HRID 857163Notes

Reaction equation

HRID 857163 reaction equation
FC(F)(F)S(O[CH:7]1[CH:11]=[C:10]([O:12][CH3:13])[C:9](=[CH:14][C:15]2[NH:16][C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:8]1)(=O)=O.C(OC([N:33]1[CH:37]=[CH:36][CH:35]=[C:34]1B(O)O)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C(OCC)(=O)C>[CH3:13][O:12][CH:10]1[C:9](=[CH:14][C:15]2[NH:16][C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:8][C:7]([C:34]2[NH:33][CH:37]=[CH:36][CH:35]=2)=[CH:11]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 86760307HCID 86760307, compound

Product 1

HCID 69362609HCID 69362609, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

The crude triflate 78 was mixed with about 3 equivalent of boronic acid 8, 8 equivalents of potassium carbonate and about 0.1 equivalent of tetrakistriphenylphosphine palladium under argon. Anhydrous 1,4-dioxane (10 mL) was added to the reaction mixture, and it was heated at 90° C. in a sand bath. After three hours, the mixture was cooled and added to ethyl acetate (100 mL). The organic layer was washed with brine (3×100 mL) and was then dried over sodium sulfate, filtered and concentrated in vacuo. The resulting crude mixture was passed through a short column of neutral alumina using 50/50 hexanes/ethyl acetate as an eluent. The relevant fractions were combined and concentrated, and the resulting crude product was purified using a preparative plate of neutral alumina and eluted using 80/20 hexanes/ethyl acetate. The alumina band containing Compound 79 was washed with ethyl acetate and concentrated to provide the Compound 79 as a red dark solid (2 mg, 20%). (500 MHz, CD3OD) : δ (ppm), 7.55 (m, 2H); 7.20 (t, 1H); 7.13 (s, 1H); 7.03 (t, 1H); 6.90 (s, 1H), 6.88 (s, 1H); 6.85 (s, 1H); 6.32 (s, 1H), 6.17 (s, 1H); 3.97 (s, 3H). MS (M+H): 290.0.

Workup

  1. temperaturethe mixture was cooled
  2. washThe organic layer was washed with brine (3×100 mL)
  3. dry with materialwas then dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. concentrationconcentrated
  7. customthe resulting crude product was purified
  8. washeluted
  9. additionThe alumina band containing Compound 79
  10. washwas washed with ethyl acetate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-03f0ec9b66fa42b698da4f936ce89fdc
Source dataset
uspto-grants-2006_12
Patent number
US07144912B2

Reaction notes

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