Sodium Carbonate → HCID 24962742, compound

HRID 244428Notes

Reaction equation

HRID 244428 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10](Br)[CH:11]=2)[C:6]([C:14]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[N:25]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[N:24]=[CH:23]3)([OH:19])[C:15]([F:18])([F:17])[F:16])=[CH:5]1)[CH:2]=[CH2:3].[NH:36]1[C:40](B(O)O)=[CH:39][CH:38]=[N:37]1.C(=O)([O-])[O-].[Na+].[Na+]>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.CN(C=O)C>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:40]3[NH:36][N:37]=[CH:38][CH:39]=3)[CH:11]=2)[C:6]([C:14]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[N:25]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[N:24]=[CH:23]3)([OH:19])[C:15]([F:18])([F:17])[F:16])=[CH:5]1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 112519791H-Pyrazole-5-boronic acidHCID 24957617HCID 24957617, compound

Product 1

HCID 24962742HCID 24962742, compoundYield 36.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In a 10 mL microwave tube charged with 100.0 mg (0.18 mmol) of 1-(1-allyl-6-bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol, 40.3 mg (0.36 mmol) of 1H-pyrazole-5-boronic acid, 57.0 mg (0.53 mmol) of sodium carbonate, 23.1 mg (0.02 mmol) of tetrakis(triphenylphosphine)palladium, and 4 mL DMF was stirred in the microwave at 120° C. for 2.5 hours. The mixture was then cooled to room temperature, quenched with saturated ammonia chloride solution, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate-hexanes (30-80% gradient). The major fractions were combined and concentrated in vacuo to afford 35.0 mg (36%) of the title compound. MS m/z 532.5 (MH+).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customquenched with saturated ammonia chloride solution
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef1b4be94ff544aa913fa4f8c0784812
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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