Butyl bromide → HCID 68894578, compound

HRID 1437183Notes

Reaction equation

HRID 1437183 reaction equation
[H-].[Na+].[CH2:3]([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].Br[CH2:24][CH2:25][CH2:26][CH3:27]>CN(C=O)C>[CH2:3]([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)[N:16]([CH2:24][CH2:25][CH2:26][CH3:27])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 49759051Ethyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate

Product 1

HCID 68894578HCID 68894578, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Under nitrogen atmosphere, over a suspension of 0.55 g (13.72 mmol) of sodium hydride 60% in paraffin oil in 10 ml of DMF, a solution of 2.5 g (9.1 mmol) of 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-piperidine-1-carboxylic acid ethyl ester in 10 ml of DMF was added. After 30 minutes, a solution of 1.2 ml of 4-bromobutane in 2 ml of DMF was added. The crude mixture was stirred at room temperature for 15 hours. The solvent was removed under reduced pressure and the crude was partionated between ethyl acetate and water. The organic phase was dried over sodium sulphate, filtered and the solvent was removed under reduced pressure affording 3.1 g of 4-(1-butyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-piperidine-1-carboxylic acid ethyl ester.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-84882e03e39f48d385cb1c2c32cac31b
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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