Ammonium Chloride → HCID 68072623, compound

HRID 1527293Notes

Reaction equation

HRID 1527293 reaction equation
[CH2:1]([Al](CC)CC)[CH3:2].Br[C:9]1[CH:10]=[C:11]2[CH:17]=[N:16][NH:15][C:12]2=[CH:13][N:14]=1.[NH4+].[Cl-]>C1COCC1.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>[CH2:1]([C:9]1[CH:10]=[C:11]2[CH:17]=[N:16][NH:15][C:12]2=[CH:13][N:14]=1)[CH3:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 16682930TriethylaluminumHCID 457897785-Bromo-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 68072623HCID 68072623, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Triethylaluminum (21.7 mL, 40.4 mmol, 25 wt % solution in toluene) was added to a vigorously stirred solution of 5-bromo-1H-pyrazolo[3,4-c]pyridine [929617-35-6] (4.00 g, 20.2 mmol) and Pd(PPh3)4 (1.17 g, 1.01 mmol) in THF (100 mL) under argon. The reaction mixture was stirred at 65° C. for 60 h. The mixture was cooled to RT and poured into sat. aq. NH4Cl. The resulting suspension was filtered, the solid was washed with water and discarded. The filtrate and combined washings were extracted with EtOAc (3×). The combined organic extracts were washed with brine, then dried (Phase separator) and concentrated under reduced pressure. The residual oil was purified by flash column chromatography on silica gel (EtOAc/c-hexane 50:50, then 75:25, then 100:0). TLC, Rf (c-hexane/EtOAc 1:3)=0.22; MS (LC-MS): 148 [M+H]+, tR (HPLC conditions k): 0.71 min.

Workup

  1. temperatureThe mixture was cooled to RT
  2. filtrationThe resulting suspension was filtered
  3. washthe solid was washed with water
  4. extractionwere extracted with EtOAc (3×)
  5. washThe combined organic extracts were washed with brine
  6. customdried (Phase separator)
  7. concentrationconcentrated under reduced pressure
  8. customThe residual oil was purified by flash column chromatography on silica gel (EtOAc/c-hexane 50:50
  9. custom0.71 min.

Sources & evidence

ORD record
ord-69784df268984f3695b893190aa0bfff
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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