Potassium Carbonate → HCID 58086316, compound

HRID 1098489Notes

Reaction equation

HRID 1098489 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[C:15](Br)[CH:16]=[C:11]2[C:10]([C:18](=[O:28])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[C:20]=2[F:27])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([C:30]3[S:29][CH:33]=[CH:32][CH:31]=3)[CH:16]=[C:11]2[C:10]([C:18](=[O:28])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[C:20]=2[F:27])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339602-Thiopheneboronic acidHCID 58086147HCID 58086147, compound

Product 1

HCID 58086316HCID 58086316, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 5-bromo-3-(2-fluoro-3-methoxy-benzoyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (86, 350.0 mg, 0.78 mmol) in tetrahydrofuran (30 mL) and water (10 mL) were added 2-thiophene boronic acid (190 mg, 1.49 mmol), tetrakis(triphenyl-phosphine)palladium(0) (40.0 mg, 0.0346 mmol) and potassium carbonate (780 mg, 5.64 mmol) under an atmosphere of nitrogen. The reaction mixture was refluxed for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated to give crude compound (87, 0.30 g, 85%).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-65caaa4769fa4bdd83ce85131b351149
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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