Sodium t-butoxide → HCID 178420309, compound

HRID 2204638Notes

Reaction equation

HRID 2204638 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[N:25][NH2:26])[C:15]2[C:20](Cl)=[CH:19][N:18]=[C:17]3[NH:22][CH:23]=[CH:24][C:16]=23)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+]>CN1C(=O)CCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:15]3=[C:16]4[CH:24]=[CH:23][NH:22][C:17]4=[N:18][CH:19]=[C:20]3[NH:26][N:25]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 23676156Sodium t-butoxideHCID 86637187HCID 86637187, compound

Product 1

HCID 178420309HCID 178420309, compoundYield 40.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-((1-benzylpiperidin-4-yl)(hydrazono)methyl)-5-chloro-1H-pyrrolo[2,3-b]pyridine (0.85 g, 2.44 mmol), sodium tert-butoxide (0.565 g, 5.87 mmol), palladium acetate (0.0055 g, 0.024 mmol) and (R)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butyl phosphine (0.0136 g, 0.0244 mmol) was heated in NMP (10 mL) at about 160° C. in a CEM Discover microwave for about 30 min. The NMP was removed under reduced pressure and the residue was partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (50 mL). The organic phase was separated, washed with brine (55 mL), dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was suspended in MeCN (10 mL) and the precipitate was collected by filtration and dried in vacuo to yield 1-(1-benzylpiperidin-4-yl)-3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridine as a tan solid (0.33 g, 40%): LC/MS (Table 2, Method n) Rt=1.42 min; MS m/z: 332 (M+H)+.

Workup

  1. customThe NMP was removed under reduced pressure
  2. customthe residue was partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (50 mL)
  3. customThe organic phase was separated
  4. washwashed with brine (55 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure
  7. filtrationthe precipitate was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-8d6a8112aded46299b91052c2f74be0b
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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