Chlorosuccinimide → HCID 86689841, compound

HRID 2409062Notes

Reaction equation

HRID 2409062 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][C:6]([C:10](=[O:12])[CH3:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl:13]N1C(=O)CCC1=O>CN(C=O)C.CCOC(C)=O>[Cl:13][C:3]1[C:4]2=[N:5][C:6]([C:10](=[O:12])[CH3:11])=[CH:7][CH:8]=[C:9]2[NH:1][CH:2]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 86689828HCID 86689828, compound

Product 1

HCID 86689841HCID 86689841, compoundYield 98.59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To 1-(1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone (2.80 g, 17.48 mmol) in anhydrous DMF (27 mL) at 0° C. was added a solution of N-chlorosuccinimide (2.50 g, 18.36 mmol) dissolved in anhydrous DMF (54 mL). The reaction mixture was stirred at 0° C. for 1 h and then at RT for 18 h. The reaction mixture was diluted with EtOAc, and the organic layer was washed with sat'd. aq. NaHCO3 solution, water and brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude residue was purified by SiO2 chromatography eluting with EtOAc/heptane. Trituration with DCM/heptane afforded 3.35 g (98.59%) of 1-(3-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone as a white solid. 1H NMR (400 MHz, DMSO) δ 11.96 (br s, 1H), 8.01 (d, J=2.9 Hz, 1H), 7.96 (d, J=8.6 Hz, 1H), 7.88 (d, J=8.6 Hz, 1H), 2.71 (s, 3H); MS (ESI) m/z: 195.2 [M+1]+.

Workup

  1. waitat RT for 18 h
  2. washthe organic layer was washed with sat'd
  3. dry with materialaq. NaHCO3 solution, water and brine, dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by SiO2 chromatography
  7. washeluting with EtOAc/heptane

Sources & evidence

ORD record
ord-f9c754b7e5244ab9959870a37897c306
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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