Potassium Carbonate → HCID 86700055, compound

HRID 1428104Notes

Reaction equation

HRID 1428104 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)O1.C(=O)([O-])[O-].[K+].[K+].Br[C:24]1[C:25]([NH2:46])=[N:26][CH:27]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)=[C:32]([O:44][CH3:45])[CH:31]=2)[CH:29]=1>O1CCOCC1.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>[NH2:13][C:12]1[CH:11]=[CH:10][C:9]([C:24]2[C:25]([NH2:46])=[N:26][CH:27]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][N:39]4[CH2:43][CH2:42][CH2:41][CH2:40]4)=[C:32]([O:44][CH3:45])[CH:31]=3)[CH:29]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 86700054HCID 86700054, compound

Product 1

HCID 86700055HCID 86700055, compoundYield 105.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (285 mg), tetrakis(triphenylphosphine)palladium (110 mg) and potassium carbonate (396 mg) were added to a solution of the compound obtained in Step 1 of Example 39 (375 mg) in dioxane (10 ml) and water (1 ml) at room temperature. The reaction mixture was stirred at 100° C. for five hours. The reaction mixture was returned to room temperature, followed by extraction with chloroform. The organic layer was dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography [chloroform:methanol=19:1 (v/v)] to give 407 mg of the title compound as an oily substance.

Workup

  1. customwas returned to room temperature
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography [chloroform:methanol=19:1 (v/v)]

Sources & evidence

ORD record
ord-87b2eb0a6cfd4052a59dae5d108aed80
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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