Water → 4-[1-(2-ethoxyethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid ethyl ester

HRID 1437162Notes

Reaction equation

HRID 1437162 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH:10]=[C: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+].[CH2:23]([O:25][CH2:26][CH2:27]Br)[CH3:24].O>CN(C=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH:8]=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:24][CH2:23][O:25][CH2:26][CH3:27])[CH:13]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl etherHCID 457902484-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid ethyl ester

Product 1

HCID 688982874-[1-(2-ethoxyethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.30 g (4.76 mmol) of 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid ethyl ester were dissolved in 11 ml of DMF and, at room temperature, 0.25 g (5.6 mmol) of 60% sodium hydride were carefully added. This mixture was stirred for half an hour at room temperature. 0.75 ml (6.0 mmol) of 2-bromoethyl ethyl ether were dropwise added and the stirring was continued for 24 hours at 60° C. The reaction mixture was cooled to room temperature and poured over cold water. This 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. The 1.46 g (74% of yield) of crude material were pure enough for the next synthetic step.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThis 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. customThe 1.46 g (74% of yield) of crude material

Sources & evidence

ORD record
ord-81ce5429d7904ac291787c2c604a285c
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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