Toluene → HCID 86761806, compound

HRID 1968387Notes

Reaction equation

HRID 1968387 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:19]3=[C:20]4[C:10](=[CH:11][CH:12]=[C:13](B(O)O)[C:14]4=[CH:15][CH:16]=[C:17]3[CH:18]=1)[CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:30]1([CH3:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>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>[C:30]1([CH:36]2[CH:36]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:7]3[CH:8]=[CH:9][C:10]([C:11]4[CH:12]=[CH:13][C:14]5[C:6]6=[C:7]7[C:19](=[CH:6][C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:18][C:17]7=[CH:16][CH:15]=5)[CH:17]=[CH:18][C:5]=46)=[CH:20][C:19]=3[C:19]3[C:7]2=[CH:8][CH:9]=[C:10]([C:11]2[CH:12]=[CH:11][C:10]4[C:20]5=[C:16]6[C:15](=[CH:6][C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:18][C:17]6=[CH:8][CH:9]=4)[CH:14]=[CH:13][C:12]=25)[CH:20]=3)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 57815993HCID 57815993, compound

Product 1

HCID 86761806HCID 86761806, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

As illustrated in Formula 7, the product 4a in Formula 6 (1.2 g, 2.46 mmol), 7-tert-butylpyren-1-ylboronic acid (2.23 g, 7.38 mmol), potassium carbonate solution (2.0 M, 10 mL), and dried toluene (30 mL) were charged in a two-necked bottle. The bottle was deoxygenated and purged with nitrogen, and the mixture in the bottle was stirred at 60° C. until it was totally dissolved. The nitrogen pressure of the bottle was increased, and Pd(PPh3)4 (289 mg, 0.25 mmol) was rapidly added into the bottle. The reaction was heated to 110° C., and stirred for 48 hours. The resulting was cooled to room temperature to precipitate a solid, and the solid was collected by filtering. The solid was sublimated at a temperature of 330° C. to obtain a white solid of 1.56 g (yield=75%).

Workup

  1. customThe bottle was deoxygenated
  2. custompurged with nitrogen
  3. dissolutionwas totally dissolved
  4. temperatureThe nitrogen pressure of the bottle was increased
  5. temperatureThe reaction was heated to 110° C.
  6. stirringstirred for 48 hours
  7. temperatureThe resulting was cooled to room temperature
  8. customto precipitate a solid
  9. customthe solid was collected
  10. filtrationby filtering
  11. customwas sublimated at a temperature of 330° C.
  12. customto obtain a white solid of 1.56 g (yield=75%)

Sources & evidence

ORD record
ord-87a2c6884dc44548bc40cd2478a8109c
Source dataset
uspto-grants-2013_04
Patent number
US08426039B2

Reaction notes

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