Potassium Carbonate → HCID 57421951, compound

HRID 2059617Notes

Reaction equation

HRID 2059617 reaction equation
[F:1][C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[CH:15]=3)=[C:7](I)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:26][CH3:27].[CH3:28][O:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[C:34]([O:38][CH3:39])[C:35]=1[O:36][CH3:37].[C:43]([O-])([O-])=[O:44].[K+].[K+]>C1(OC)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[CH:15]=3)=[C:7]([C:43](=[O:44])[C:32]3[CH:31]=[C:30]([O:29][CH3:28])[C:35]([O:36][CH3:37])=[C:34]([O:38][CH3:39])[CH:33]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:26][CH3:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 57421950HCID 57421950, compound

Product 1

HCID 57421951HCID 57421951, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 7519AnisoleSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 4-(7-fluoro-3-iodo-6-methoxy-benzofuran-2-yl)-1-(4-methoxybenzyl)-1H-pyrazole (0.087 g, 0.182 mmol), 3,4,5-trimethoxyphenyl boronic acid (0.058 g, 0.27 mmol), dry K2CO3 (0.075 g, 0.55 mmol) and Pd(PPh3)2Cl2 (0.016 g, 0.014 mmol) in anhydrous anisole (8 ml) was placed in Parr mini bench top reactor (series 4561, 300 ml. The reactor was degassed under reduced pressure and flashed with dry N2 than flashed three times with CO by pressurizing the reactor up to 180 psi and depressurizing. Finally, the reactor was pressurized to 180 psi and stirred at 85±5° C. (the temperature of external oil bath) for ˜30 h. The reactor was cooled down to room temperature and the reaction mixture was diluted to 20 ml with CH2Cl2 and filtered through celite. The celite pad was washed with fresh portion of CH2Cl2 (3×20 ml) and combined filtrates were evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography (silica-gel, eluted with CH2Cl2/ethyl acetate 9:1) giving the product of Step 1 as a creamy solid (0.05 g, 50.25%) 1H NMR (300 MHz, CDCl3) 7.98 (s, 1H), 7.97 (s, 1H), 7.08 (s, 2H), 6.9-6.97 (m, 1H), 6.82-6.86 (m, 1H), 5.21 (s, 2H), 3.7-3.96 (m, 15H).

Workup

  1. customThe reactor was degassed under reduced pressure
  2. temperatureThe reactor was cooled down to room temperature
  3. additionthe reaction mixture was diluted to 20 ml with CH2Cl2
  4. filtrationfiltered through celite
  5. washThe celite pad was washed with fresh portion of CH2Cl2 (3×20 ml)
  6. customwere evaporated to dryness under reduced pressure
  7. customThe residue was purified by flash column chromatography (silica-gel, eluted with CH2Cl2/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-99835d6c268247aa9345ebdde6faac3e
Source dataset
uspto-grants-2012_10
Patent number
US08278290B2

Reaction notes

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