Triethylamine → HCID 178505620, compound

HRID 1875437Notes

Reaction equation

HRID 1875437 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[NH:10][N:9]=[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:5]2=[N:6][CH:7]=1.C(N(CC)CC)C>C(O)C.C1COCC1.[Pd]>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][C:8]1[C:5]2=[N:6][CH:7]=[CH:2][CH:3]=[C:4]2[NH:10][N:9]=1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 178505619HCID 178505619, compound

Product 1

HCID 178505620HCID 178505620, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

411 mg (1.57 mmol) of 6-chloro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridine from example 3A are dissolved in a mixture of 4 ml of ethanol and 4 ml of THF, and, after addition of 159 mg (1.57 mmol) of triethylamine and 140 mg of 10% palladium on carbon, the mixture is hydrogenated under a hydrogen atmosphere at atmospheric pressure for 2 h. It is then filtered to remove the catalyst, concentrated in vacuo and taken up in water. The mixture is extracted with dichloromethane, and the organic phase is dried over sodium sulfate. Concentration results in 334 mg (94% of theory) of the title compound as white crystals.

Workup

  1. filtrationIt is then filtered
  2. customto remove the catalyst
  3. concentrationconcentrated in vacuo
  4. extractionThe mixture is extracted with dichloromethane
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. concentrationConcentration

Sources & evidence

ORD record
ord-fc86dcb1e9fe489282a5ba655da449ce
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

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