Sodium hydride → 4-(1-furan-3-ylmethyl-1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylic acid tert-butyl ester

HRID 1437170Notes

Reaction equation

HRID 1437170 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:26][C:27]1[CH:31]=[CH:30][O:29][CH:28]=1>CN(C=O)C.C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:26][C:27]3[CH:31]=[CH:30][O:29][CH:28]=3)[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 110949343-(Bromomethyl)furanHCID 49758876tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate

Product 1

HCID 688949704-(1-furan-3-ylmethyl-1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Under nitrogen atmosphere, 1.14 g (3.76 mmol) of 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-piperidine-1-carboxylic acid tert-butyl ester were dissolved in 30 ml of anhydrous DMF and, at room temperature, carefully added to a suspension containing 0.24 g (6.05 mmol) of 60% sodium hydride. This mixture was stirred for 30 minutes and 8.2 ml (4.92 mmol) of a freshly prepared 0.6 M solution of 3-bromomethylfuran in ethyl ether were dropwise added and the reaction mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and the crude mixture was extracted between ethyl acetate and water. The organic phase was washed with water and brine, dried with magnesium sulphate, filtered and evaporated to dryness. The crude mixture was purified by flash chromatography over silica gel affording 1.4 g (97% of yield) of the expected product.

Workup

  1. additioncarefully added to a suspension
  2. stirringthe reaction mixture was stirred at room temperature for 16 hours
  3. customThe solvent was removed under reduced pressure
  4. extractionthe crude mixture was extracted between ethyl acetate and water
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried with magnesium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe crude mixture was purified by flash chromatography over silica gel affording 1.4 g (97% of yield) of the expected product

Sources & evidence

ORD record
ord-72038a6b5c9f4e139c41d369c24f77d1
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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