Potassium Carbonate → HCID 58087770, compound

HRID 1964999Notes

Reaction equation

HRID 1964999 reaction equation
[F:1][CH:2]([F:26])[O:3][C:4]1[CH:5]=[C:6]([C:14]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[C:22](Br)[CH:23]=3)[NH:18][CH:17]=2)=[O:15])[CH:7]=[C:8]([O:10][CH:11]([F:13])[F:12])[CH:9]=1.[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.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>[F:1][CH:2]([F:26])[O:3][C:4]1[CH:5]=[C:6]([C:14]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[C:22]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:23]=3)[NH:18][CH:17]=2)=[O:15])[CH:7]=[C:8]([O:10][CH:11]([F:13])[F:12])[CH:9]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 58086139HCID 58086139, compound

Product 1

HCID 58087770HCID 58087770, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To (3,5-Bis-difluoromethoxy-phenyl)-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (P-1519, 29.0 mg, 0.067 mmol) in acetonitrile (4.0 mL) were added phenylboronic acid (12.2 mg, 0.10 mmol), Tetrakis(triphenylphosphine)palladium(0) (10.0 mg, 8.65E-6 mol) and 1.0 M potassium carbonate in water (1.5 mL). The reaction was microwaved (300 watts) at 160° C. for 7 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated, and purified with silica gel column chromatography to give the compound as a white solid (P-1521, 9.4 mg, 33%). MS (ESI) [M+H+]+=431.2.

Workup

  1. customThe reaction was microwaved (300 watts) at 160° C. for 7 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified with silica gel column chromatography

Sources & evidence

ORD record
ord-6b08a653db6449b59c6aae6c779a3c0e
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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