Chlorosuccinimide → HCID 86689841, compound

HRID 2409025Notes

Reaction equation

HRID 2409025 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.C1C(=O)N([Cl:20])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Cl:20][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 95.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution 1-(1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone (517.0 mg, 3.23 mmol) in anhydrous DMF (5.0 mL) at 0° C. was added a solution of NCS (462.0 mg, 3.39 mmol) dissolved in anhydrous DMF (10 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 in vacuo. The crude residue was purified by SiO2 chromatography eluting with EtOAc/heptane. Recovered product was crystallized from DCM to afford 600 mg (95.5%) of 1-(3-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone as a white solid: 1H NMR (400 MHz, DMSO-d6) 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 in vacuo
  6. customThe crude residue was purified by SiO2 chromatography
  7. washeluting with EtOAc/heptane
  8. customRecovered product was crystallized from DCM

Sources & evidence

ORD record
ord-894a1031a82e4427a1ec1390ce4f1740
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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