Water → 4-[1-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidine-1-carboxylic acid ethyl ester

HRID 1437155Notes

Reaction equation

HRID 1437155 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H-].[Na+].Br[CH2:24][CH2:25][O:26][CH3:27].O>CN(C=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:24][CH2:25][O:26][CH3:27])[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 49759051Ethyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate

Product 1

HCID 688944194-[1-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g (3.66 mmol) of 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylic acid ethyl ester were dissolved in 10 ml of DMF and, at room temperature, 0.19 g (4.76 mmol) of 60% sodium hydride were carefully added. This mixture was stirred for half an hour. 0.45 ml (5.12 mmol) of 1-bromo-2-methoxyethane were added dropwise and the mixture was further stirred for 24 hours at 60° C. The reaction mixture was cooled to room temperature and poured over cold water. The aqueous phase was extracted twice with dichloromethane and the organic phase was washed with water and brine, dried with magnesium sulphate, filtered and evaporated to dryness. This resulted in 0.86 g (71% of yield) of product.

Workup

  1. stirringthe mixture was further stirred for 24 hours at 60° C
  2. extractionThe aqueous phase was extracted twice with dichloromethane
  3. washthe organic phase was washed with water and brine
  4. dry with materialdried with magnesium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThis resulted in 0.86 g (71% of yield) of product

Sources & evidence

ORD record
ord-3e6d48007ffa4e75a7b0bd55a6579385
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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