Potassium Carbonate → HCID 118468018, compound

HRID 63598Notes

Reaction equation

HRID 63598 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13](Br)[CH:14]=3)[N:9]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>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.C1(C)C=CC=CC=1.C(O)C>[C:1]1([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([C:31]4[CH:32]=[CH:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=4)[CH:14]=3)[N:9]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 70952154HCID 70952154, compound

Product 1

HCID 118468018HCID 118468018, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3-phenyl-5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (309 mg, 0.75 mmol) in a 3:1 toluene/ethanol mixture (24 ml) are added 2-methoxy-benzene boronic acid (125 mg, 0.83 mmol), K2CO3 (2.4 ml of 2 M solution in water, 4.5 mmol), Pd(PPh3)4 (1.5 mol %), and the mixture is heated at 85° C. for 2 hours under argon. The mixture is cooled to room temperature, concentrated under a vacuum and redissolved in a water/CH2Cl2 mixture. The aqueous phase is extracted several times with CH2Cl2 and the combined organic phases are dried on MgSO4. The solvent is evaporated under reduced pressure and the residue purified by flash chromatography on silica gel (100% CH2Cl2) to yield the purified product in the form of a colorless oil with a yield of 98%.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. concentrationconcentrated under a vacuum
  3. dissolutionredissolved in a water/CH2Cl2 mixture
  4. extractionThe aqueous phase is extracted several times with CH2Cl2
  5. customthe combined organic phases are dried on MgSO4
  6. customThe solvent is evaporated under reduced pressure
  7. customthe residue purified by flash chromatography on silica gel (100% CH2Cl2)
  8. customto yield the purified product in the form of a colorless oil with a yield of 98%

Sources & evidence

ORD record
ord-dd169ea86f934a97b25c6ab5bfbae715
Source dataset
uspto-grants-2016_09
Patent number
US09447093B2

Reaction notes

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