N,N,N',N'-Tetramethylethylenediamine → HCID 86657498, compound

HRID 2359011Notes

Reaction equation

HRID 2359011 reaction equation
CN(C)CCN(C)C.C([Li])CCC.[C:14]([O:18][C:19](=[O:28])[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[N:22]=1)([CH3:17])([CH3:16])C.[N+:29]([C:32]1[CH:33]=[C:34]2[C:38](=[CH:39][CH:40]=1)CC(=O)C2)([O-:31])=[O:30]>C1COCC1>[Cl:27][C:23]1[CH:24]=[CH:25][C:26]2[C:14]3([CH2:16][C:34]4[C:38](=[CH:39][CH:40]=[C:32]([N+:29]([O-:31])=[O:30])[CH:33]=4)[CH2:17]3)[O:18][C:19](=[O:28])[NH:20][C:21]=2[N:22]=1

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 15020665-Nitro-2-indanoneHCID 11253185tert-butyl N-(6-chloropyridin-2-yl)carbamateHCID 178418339Butyllithium

Product 1

HCID 86657498HCID 86657498, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

A solution of N,N,N′,N′-tetramethylethylenediamine (3.3 mL, 22 mmol) in THF (8 mL) is cooled to −20° C. and treated with n-butyllithium (2.5 Min hexanes, 8.8 mL, 22 mmol) over 10 min. After stirring for 30 min, the mixture is cooled to −78° C. and treated with a solution of tert-butyl(6-chloropyridin-2-yl)carbamate (2.29 g, 10 mmol) [Williams US2006/028835] in THF (6 mL) over 15 min. After 1 h, the mixture is warmed to −50° C. and treated with a solution of 5-nitro-1,3-dihydro-2H-inden-2-one (2.66 g, 15 mmol) in THF (8 mL) over 10 min. The mixture is then allowed to warm to rt and stirred for 24 h. The reaction is quenched by addition of saturated aqueous NaHCO3 and the mixture is then extracted with EtOAc (×3). The combined organic extracts are washed successively with water and brine, dried (anhydrous MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography (gradient elution with hexanes-EtOAc) to afford the title compound.

Workup

  1. waitAfter 1 h
  2. temperaturethe mixture is warmed to −50° C.
  3. temperatureto warm to rt
  4. stirringstirred for 24 h
  5. customThe reaction is quenched by addition of saturated aqueous NaHCO3
  6. extractionthe mixture is then extracted with EtOAc (×3)
  7. washThe combined organic extracts are washed successively with water and brine
  8. dry with materialdried (anhydrous MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue is purified by silica gel chromatography (gradient elution with hexanes-EtOAc)

Sources & evidence

ORD record
ord-3bdc52f728f84aa7b12657d803735cd5
Source dataset
uspto-grants-2014_04
Patent number
US08685965B2

Reaction notes

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