HCID 118380514, compound → HCID 118380527, compound

HRID 627029Notes

Reaction equation

HRID 627029 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]>[Pd].CCO>[CH3:1][CH:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[CH:3]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

4

Reactant 1

HCID 118380514HCID 118380514, compound

Product 1

HCID 118380527HCID 118380527, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 100 mL round-bottomed flask, 1-tert-butyl 2-ethyl 3-methyl-1H-pyrrolo[2,3-b]pyridine-1,2-dicarboxylate (235 mg, 772 μmol, Eq: 1.00) was combined with EtOH (34 mL) to give a colorless solution. 10% Palladium on carbon (82.2 mg, 77.2 μmol, Eq: 0.1) was added and the reaction was stirred under a hydrogen atmosphere (balloon) at rt overnight. The reaction mixture was filtered through Celite and concentrated in vacuo to give 1-tert-butyl 2-ethyl 3-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1,2-dicarboxylate (235 mg), m/z=307 (M+H).

Workup

  1. customto give a colorless solution
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ab26c34b22c4ab39db1c4b1a895d153
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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