Trifluoroacetic acid → Diethyl 1-(3-amino-2,2-dimethylpropyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

HRID 1521704Notes

Reaction equation

HRID 1521704 reaction equation
C(OC([NH:8][CH2:9][C:10]([CH3:32])([CH3:31])[CH2:11][N:12]1[C:16]2=[N:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:20]=[C:15]2[CH:14]=[C:13]1[C:26]([O:28][CH2:29][CH3:30])=[O:27])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][C:10]([CH3:31])([CH3:32])[CH2:11][N:12]1[C:16]2=[N:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:20]=[C:15]2[CH:14]=[C:13]1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67238212Diethyl 1-{3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropyl}-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

Product 1

HCID 67237221Diethyl 1-(3-amino-2,2-dimethylpropyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylateYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl 1-{3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropyl}-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (4.20 g, 9.39 mmol) in CH2Cl2 (20 mL) is added TFA (10 mL). The mixture is stirred at room temperature for 4 hr. The solvent is evaporated and the residue is partitioned between ethyl acetate and saturated NaHCO3 solution. The layers are separated and the aqueous layer is further extracted with ethyl acetate. The combined organic phases are washed with brine, and are dried (Na2SO4) and concentrated in vacuo to afford the title compound (3.30 g, quantitative). LCMS: 348.79 (M+H+).

Workup

  1. customThe solvent is evaporated
  2. customthe residue is partitioned between ethyl acetate and saturated NaHCO3 solution
  3. customThe layers are separated
  4. extractionthe aqueous layer is further extracted with ethyl acetate
  5. washThe combined organic phases are washed with brine
  6. dry with materialare dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-91e299f017ff47199f02ae073b4f40b9
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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