Potassium Carbonate → HCID 66991490, compound

HRID 475449Notes

Reaction equation

HRID 475449 reaction equation
[CH3:1][CH:2]([CH3:30])[C@H:3]([NH:8][C:9]([C:11]1[O:15][C:14]([C:16]2[N:21]=[CH:20][C:19](OS(C(F)(F)F)(=O)=O)=[CH:18][CH:17]=2)=[CH:13][CH:12]=1)=[O:10])[C:4](=[O:7])[NH:5][CH3:6].[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][CH:2]([CH3:30])[C@H:3]([NH:8][C:9]([C:11]1[O:15][C:14]([C:16]2[CH:17]=[CH:18][C:19]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:20][N:21]=2)=[CH:13][CH:12]=1)=[O:10])[C:4](=[O:7])[NH:5][CH3:6]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 86659070HCID 86659070, compound

Product 1

HCID 66991490HCID 66991490, compound

Conditions

Temperature
100 °C

Procedure

A flask charged with trifluoromethanesulfonic acid 6-[5-((S)-2-methyl-1-methylcarbamoyl-propylcarbamoyl)-furan-2-yl]-pyridin-3-yl ester (50 mg, 0.11 mmol), phenylboronic acid (27 mg, 0.22 mmol), palladiumtetrakistriphenylphosphine (13 mg, 0.01 mmol), and potassium carbonate (61 mg, 0.44 mmol) is flushed with argon. Toluene (2 mL), ethanol (0.5 mL), and water (1 mL) are added and the reaction is stirred at 100° C. for 2 hours. The reaction is cooled to room temperature, ethyl acetate (10 mL), is added and the mixture washed with water (10 mL), brine (10 mL), and dried over MgSO4. The solution is filtered and evaporated in vacuo to give an oil that is purified by preparative HPLC. 5-(5-Phenyl-pyridin-2-yl)-furan-2-carboxylic acid ((S)-2-methyl-1-methylcarbamoyl-propyl)-amide is obtained as a white solid, 16 mg, 38%, LC/MS ESI m/z (M+H)+=377.43.

Workup

  1. customis flushed with argon
  2. additionToluene (2 mL), ethanol (0.5 mL), and water (1 mL) are added
  3. temperatureThe reaction is cooled to room temperature
  4. additionethyl acetate (10 mL), is added
  5. washthe mixture washed with water (10 mL), brine (10 mL)
  6. dry with materialdried over MgSO4
  7. filtrationThe solution is filtered
  8. customevaporated in vacuo
  9. customto give an oil that
  10. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-2fe2342826df4f37a55d8ee076244c54
Source dataset
uspto-grants-2014_01
Patent number
US08637550B2

Reaction notes

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