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N,N'-Dimethylethylenediamine → tert-butyl 4-[1-methyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxopiperazine-1-carboxylate

HRID 1622883
Notes
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Reaction equation

HRID 1622883 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:8][CH:9]=2)[N:4]([CH3:19])[CH:3]=1.[O:20]=[C:21]1[NH:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>[Cu]I.O.O1CCOCC1>[CH3:19][N:4]1[C:5]2=[N:6][C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:8][CH:9]=[C:10]2[C:2]([N:26]2[CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[CH2:22][C:21]2=[O:20])=[CH:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 678161163-Bromo-1-methyl-6-(2-pyridylmethoxy)pyrrolo[2,3-b]pyridine

Product 1

HCID 67817033tert-butyl 4-[1-methyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxopiperazine-1-carboxylate
Yield 88.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-1-methyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridine (0.226 g, 0.71 mmol), tert-butyl 3-oxopiperazine-1-carboxylate (0.20 g, 1 mmol), copper (I) iodide (0.027 g, 0.142 mmol) and potassium phosphate (0.212 g, 1 mmol) is purged under a nitrogen atmosphere in a reaction tube. 1,4-Dioxane (3 mL) and N,N′-dimethylethylene diamine (0.031 mL, 0.288 mmol) are added, the tube sealed and the reaction mixture heated at 100° C. for 25 h. The reaction is cooled to room temperature, poured into water and extracted with EtOAc. The organic phase is dried over sodium sulphate, filtered and concentrated in vacuo. The residue is purified by column chromatography on silica eluting with hexane/EtOAc (1:1), followed by neat EtOAc, to give the title compound (0.275 g, 0.629 mmol) as a pale yellow solid. MS (m/z): 438 (M+1).

Workup

  1. customis purged under a nitrogen atmosphere in a reaction tube
  2. customthe tube sealed
  3. temperatureThe reaction is cooled to room temperature
  4. extractionextracted with EtOAc
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography on silica eluting with hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-47d3311da1d04c9a894a4162a7096a65
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08778946B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes