Diisopropylethylamine → HCID 67434519, compound

HRID 931380Notes

Reaction equation

HRID 931380 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][Si:11]([CH3:27])([CH3:26])[CH2:12][CH2:13][O:14][CH2:15][N:16]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[CH2:18][C:17]1=[O:25].Br[CH2:29][C:30]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:31]=1[C:32](Cl)=[O:33]>C1COCC1>[N+:39]([C:36]1[CH:35]=[C:31]2[C:30]([CH2:29][C:18]3([C:32]2=[O:33])[C:19]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[N:16]([CH2:15][O:14][CH2:13][CH2:12][Si:11]([CH3:27])([CH3:26])[CH3:10])[C:17]3=[O:25])=[CH:38][CH:37]=1)([O-:41])=[O:40]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 574588861-{[2-(Trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-oneHCID 58458881HCID 58458881, compound

Product 1

HCID 67434519HCID 67434519, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N,N-Diisopropylethylamine (3.64 mL, 22 mmol) is added to a stirred solution of 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (prepared according to the procedures described in WO2008/020902) (2.64 g, 10 mmol) in THF (75 mL) at ambient temperature. To the stirred mixture is added dropwise a solution of 2-(bromomethyl)-5-nitrobenzoyl chloride (3.06 g, 11 mmol) [Pifferi et al. (1966) Tetrahedron 22, 2107] in THF (75 mL) and the mixture is then stirred at ambient temperature for 18 h. The mixture is then partitioned between EtOAc and saturated aqueous NaHCO3. The layers are separated and the aqueous layer further extracted with EtOAc. The combined organic extracts are washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue is purified by silica gel chromatography (gradient elution with hexanes-EtOAc) to afford the title compound.

Workup

  1. customprepared
  2. customat ambient temperature
  3. customThe mixture is then partitioned between EtOAc and saturated aqueous NaHCO3
  4. customThe layers are separated
  5. extractionthe aqueous layer further extracted with EtOAc
  6. washThe combined organic extracts are washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by silica gel chromatography (gradient elution with hexanes-EtOAc)

Sources & evidence

ORD record
ord-292779559f674d01b9fd7c21c7777586
Source dataset
uspto-grants-2016_03
Patent number
US09296750B2

Reaction notes

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