Potassium Carbonate → HCID 59762332, compound

HRID 40139Notes

Reaction equation

HRID 40139 reaction equation
FC(F)(F)S(O[C:7]1[CH:15]=[C:14]2[C:10]([C:11]([C:26](=[O:37])[NH:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[C:31]([F:36])[CH:30]=3)=[C:12]([CH:23]([CH3:25])[CH3:24])[N:13]2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:9][CH:8]=1)(=O)=O.[N:40]1[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=1.C([O-])([O-])=O.[K+].[K+].[Li+].[Cl-]>C1(C)C=CC=CC=1.CO.CCOC(C)=O.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.O>[CH2:16]([N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[C:7]([C:43]3[CH:44]=[CH:45][N:40]=[CH:41][CH:42]=3)[CH:15]=2)[C:11]([C:26]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[C:31]([F:36])[CH:30]=2)=[O:37])=[C:12]1[CH:23]([CH3:25])[CH3:24])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

10

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 2734379(Pyridin-4-yl)boronic acidHCID 597623021-Benzyl-3-(3,4-difluorobenzylcarbamoyl)-2-isopropyl-1H-indol-6-yl trifluoromethanesulfonate2×

Product 1

HCID 59762332HCID 59762332, compound

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

General Procedure W. A mixture of 1-benzyl-3-(3,4-difluorobenzylcarbamoyl)-2-isopropyl-1H-indol-6-yl trifluoromethanesulfonate (Compound 160, 50 mg, 0.088 mmol), pyridin-4-ylboronic acid (22 mg, 0.18 mmol), Pd(PPh3)4 (5.0 mg, 0.0043 mmol), K2CO3 (61 mg, 0.44 mmol), and LiCl (19 mg, 0.44 mmol) in toluene (3 ml), MeOH (1 ml), and H2O (0.5 ml) was heated at 90° C. for 16 h. The reaction was then cooled to room temperature, diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes) to yield the title compound.

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes)

Sources & evidence

ORD record
ord-44e6376359eb4a4b9595311267a84bdd
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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