2-[hydroxy-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-methyl]-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester → 2-propyl-2-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1895022Notes

Reaction equation

HRID 1895022 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH:16]([OH:36])[C:17]1[CH:18]=[C:19]2[CH:25]=[CH:24][N:23]([Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])[C:20]2=[N:21][CH:22]=1)[CH2:13][CH2:14][CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:13][CH2:14][CH3:15])[C:16]([C:17]1[CH:18]=[C:19]2[CH:25]=[CH:24][N:23]([Si:26]([CH:30]([CH3:32])[CH3:31])([CH:33]([CH3:34])[CH3:35])[CH:27]([CH3:28])[CH3:29])[C:20]2=[N:21][CH:22]=1)=[O:36])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 666875152-[hydroxy-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-methyl]-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 666874762-propyl-2-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-[hydroxy-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-methyl]-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.528 g, 1.03 mmol) in DCM (15 mL) at ambient temperature under nitrogen was added DMP (0.652 g, 1.54 mmol) in a single portion. After 90 minutes the reaction mixture was diluted with DCM, washed with 1 N NaOH and brine, then dried (MgSO4), filtered and concentrated in vacuo to a brown oil. Purification by chromatography (silica, 5 to 10% EtOAc in hexanes) gave 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, 79%) as a yellow gum.

Workup

  1. washwashed with 1 N NaOH and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a brown oil
  5. customPurification by chromatography (silica, 5 to 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3cc99161bfb2418faac00bdf275edcf3
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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