(S)-tert-Butyl (1-(6-(3,6-dihydro-2H-pyran-4-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate → (S)-tert-Butyl (1-(1-methyl-6-(tetrahydro-2H-pyran-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate

HRID 75304Notes

Reaction equation

HRID 75304 reaction equation
[H][H].[O:3]1[CH2:8][CH:7]=[C:6]([C:9]2[CH:10]=[C:11]3[N:27]([CH3:28])[CH:26]=[CH:25][C:12]3=[N:13][C:14]=2[C@@H:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH3:16])[CH2:5][CH2:4]1>CO.[OH-].[OH-].[Pd+2]>[CH3:28][N:27]1[C:11]2[C:12](=[N:13][C:14]([C@@H:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH3:16])=[C:9]([CH:6]3[CH2:7][CH2:8][O:3][CH2:4][CH2:5]3)[CH:10]=2)[CH:25]=[CH:26]1

Participants

5

Reactant 2

HCID 86708002(S)-tert-Butyl (1-(6-(3,6-dihydro-2H-pyran-4-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 86708003(S)-tert-Butyl (1-(1-methyl-6-(tetrahydro-2H-pyran-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a 100 mL round-bottom flask fitted with a 3-way valve and a hydrogen-filled balloon, were added (S)-tert-butyl (1-(6-(3,6-dihydro-2H-pyran-4-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate (1.23 g, 3.44 mmol) in MeOH (20 mL) along with palladium hydroxide on carbon (0.097 g, 0.688 mmol). The flask was evacuated and hydrogen introduced via the three-way valve. The reaction mixture was stirred overnight at RT. The next day an additional equivalence of Pd(OH)2 was added and the reaction mixture was stirred overnight. The reaction mixture was subsequently diluted with EtOAc, filtered through a pad of Celite, and concentrated to give the title compound as a yellow oil, which was used without further purification.

Workup

  1. customTo a 100 mL round-bottom flask fitted with a 3-way valve
  2. customThe flask was evacuated
  3. additionhydrogen introduced via the three-way valve
  4. additionThe next day an additional equivalence of Pd(OH)2 was added
  5. stirringthe reaction mixture was stirred overnight
  6. additionThe reaction mixture was subsequently diluted with EtOAc
  7. filtrationfiltered through a pad of Celite
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-af478170945142deb5ab97ffc8347d45
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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