Tetramethylammonium fluoride → 2-propyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 661547Notes

Reaction equation

HRID 661547 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:34][CH2:35][CH3:36])[C:13]([C:15]1[CH:16]=[C:17]2[CH:23]=[CH:22][N:21]([Si](C(C)C)(C(C)C)C(C)C)[C:18]2=[N:19][CH:20]=1)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+](C)(C)C.[F-]>C1COCC1.C([O-])(O)=O.[Na+].O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:34][CH2:35][CH3:36])[C:13]([C:15]1[CH:16]=[C:17]2[CH:23]=[CH:22][NH:21][C:18]2=[N:19][CH:20]=1)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 67803Tetramethylammonium fluorideHCID 666874762-propyl-2-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 666883852-propyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 86%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 2-propyl-2-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.415 g, 0.809 mmol) in THF (7.5 mL) at ambient temperature under nitrogen was added TMAF (0.753 g, 8.09 mmol). The reaction mixture was stirred for one hour, then diluted with saturated aqueous NaHCO3 (30 mL) and water (15 mL) and extracted with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to a pale yellow gum. Purification by chromatography (silica, 50 to 100% EtOAc in hexanes) gave 2-propyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.247 g, 0.692 mmol, 86%) as a colourless foam.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a pale yellow gum
  6. customPurification by chromatography (silica, 50 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1b7af6127ab44d9eba0ecfe7a45452cc
Source dataset
uspto-grants-2011_12
Patent number
US08084623B2

Reaction notes

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