Sodium Carbonate → HCID 70991880, compound

HRID 230144Notes

Reaction equation

HRID 230144 reaction equation
[C:1]([N:8]1[C:16]2[CH:15]=[C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])[N:13]=[CH:12][C:11]=2[C:10](I)=[N:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.CO.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>[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:10]1[C:11]2[CH:12]=[N:13][C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])=[CH:15][C:16]=2[N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[N:9]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 68878486HCID 68878486, compound

Product 1

HCID 70991880HCID 70991880, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

A solution of 1-BOC-6-(2,4-difluorophenoxy)-3-iodo-1H-pyrazolo[4,3-c]pyridine (0.071 g) and 2-chlorophenylboronic acid in 5 mL of benzene and 1 mL of methanol was stirred at room temperature for 15 minutes. To this solution was added tetrakis(triphenylphosphine)palladium catalyst (52 mg) and 0.3 mL of 1 M sodium carbonate. The resulting mixture was heated to reflux for five hours, cooled, filtered and the organic layer was separated. The organic layer was washed, dried and concentrated. The residue was purified via chromatography using 5% ethyl acetate in hexane as the eluent to afford 45 mg of 3-(2-chlorophenyl)-6-(2,4-difluorophenoxy)-pyrazolo[4,3-c]pyridine-1-carboxylic acid, tert-butyl ester (66% yield). Mass. Spec. M+H=458.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for five hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe organic layer was separated
  6. washThe organic layer was washed
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified via chromatography

Sources & evidence

ORD record
ord-76749161d12b46fd8de33b77142beae2
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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