Potassium Carbonate → HCID 58238625, compound

HRID 1037654Notes

Reaction equation

HRID 1037654 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[C:9]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH2:21])[N:15]=2)[CH:11]=[CH:12][CH:13]=1.[C:37]1(B(O)O)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O.O1CCOCC1.C(OCC)(=O)C.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>[F:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][O:28][C:9]2[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH2:21])[N:15]=3)=[CH:11][CH:12]=[CH:13][C:8]=2[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:31][CH:32]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 58238621HCID 58238621, compound

Product 1

HCID 58238625HCID 58238625, compoundYield 94%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Potassium carbonate (1.44 g, 10.5 mmol, 3.0 equiv) was dissolved in water (15 mL) and added to compound 9 (1.6 g, 3.5 mmol, 1.0 equiv) and phenylboronic acid (0.57 g, 4.2 mmol, 1.2 equiv) in dioxane (30 mL). A stream of nitrogen was bubbled through the solution for 15 min and tetrakis(triphenylphosphine)palladium(0) (0.02 g, 0.02 mmol, 0.005 equiv) was added to the reaction. The reaction was refluxed for 2 hr at which point LC/MS and TLC indicated the reaction to be complete. The reaction was allowed to cool to room temperature, diluted with ethyl acetate (50 mL), the organic layer was separated and washed with saturated brine (50 mL). The organic layer was dried over sodium sulfate and absorbed onto silica gel (5 g) by concentration under reduced pressure. This material was purified on a silica gel column (30 g) by eluting with ethyl acetate (1%) in heptanes (200 mL), ethyl acetate (2%) in heptanes (200 mL), ethyl acetate (3%) in heptanes (200 mL) and ethyl acetate (4%) in heptanes (200 mL). The desired product was isolated pure in 94% yield (1.5 g).

Workup

  1. customA stream of nitrogen was bubbled through the solution for 15 min
  2. temperatureThe reaction was refluxed for 2 hr at which point LC/MS and TLC
  3. customthe reaction
  4. customthe organic layer was separated
  5. washwashed with saturated brine (50 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customabsorbed onto silica gel (5 g) by concentration under reduced pressure
  8. customThis material was purified on a silica gel column (30 g)
  9. washby eluting with ethyl acetate (1%) in heptanes (200 mL), ethyl acetate (2%) in heptanes (200 mL)

Sources & evidence

ORD record
ord-1db6c68061df44de87bb546fb0bb9499
Source dataset
uspto-grants-2013_10
Patent number
US08546501B2

Reaction notes

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