Water → 2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-6-yl)-isoindole-1,3-dione

HRID 1396364Notes

Reaction equation

HRID 1396364 reaction equation
[NH:1]1[C:5]2=[N:6][C:7]([N:10]3[C:18](=[O:19])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]3=[O:20])=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.IC.[C:23](=O)([O-])[O-].[Cs+].[Cs+].O>C(#N)C>[CH3:23][N:1]1[C:5]2=[N:6][C:7]([N:10]3[C:18](=[O:19])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]3=[O:20])=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 866897262-(1H-pyrrolo[2,3-b]pyridin-6-yl)-isoindole-1,3-dione

Product 1

HCID 866897272-(1-methyl-1H-pyrrolo[2,3-b]pyridin-6-yl)-isoindole-1,3-dioneYield 117%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(1H-Pyrrolo[2,3-b]pyridin-6-yl)-isoindole-1,3-dione (179 mg, 0.68 mmol) was suspended in acetonitrile (3.4 mL). Iodomethane (53 μL, 0.843 mmol) and cesium carbonate (443 mg, 1.36 mmol) were then added. After 16 h, water was added and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried (sodium sulfate), filtered and concentrated in vacuo to give 2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-6-yl)-isoindole-1,3-dione (0.22 g, 117%) as a light brown solid, which was used directly in the next step without further purification. LCMS (EI/CI) m/z: 278 [M+H].

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df558e1c93e541a5aaad13e82bb41de6
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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