Water → HCID 59198429, compound

HRID 1971013Notes

Reaction equation

HRID 1971013 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH:11]=[CH:12][NH:13][C:14](=[O:15])[C:5]=3[C:4]=2[CH:3]=1.C1C(=O)N([Br:23])C(=O)C1.[Al].O>CN(C=O)C>[Br:23][C:11]1[C:6]2[NH:7][C:8]3[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=3[C:5]=2[C:14](=[O:15])[NH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 5359268AluminumHCID 59198430HCID 59198430, compound

Product 1

HCID 59198429HCID 59198429, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 8-fluoro-2,5-dihydro-1H-pyrido[4,3-b]indol-1-one (46 g, 228 mmol) in DMF (370 mL) was added NBS (44.5 g, 250 mmol) in small portions at 0° C. The reaction mixture was covered with aluminum foil and left to stir at room temperature overnight. The reaction mixture was treated with water (460 mL), left to stir for 3 h, filtered, and washed with water. The cake was dissolved in MeOH and filtered to remove residual solids. The filtrate was treated with charcoal, and warmed to 40° C. for 2 h. The mixture was cooled to room temperature, filtered through a pad of Celite, and concentrated. The residue was treated with isopropanol and heptane, filtered, and washed with MTBE to afford the title compound as the isopropanol solvate. 1H NMR (600 MHz, CD3SOCD3) 3 12.03 (s, 1H); 11.47 (s, 1H); 7.71 (dd, 1H); 7.59 (s, 1H); 7.52 (dd, 1H); 7.17 (dt, 1H). LRMS (APCI) calc'd for (C11H6BrFN2O) [M+H]+, 281.0. found 280.9.

Workup

  1. waitleft
  2. waitleft
  3. stirringto stir for 3 h
  4. filtrationfiltered
  5. washwashed with water
  6. dissolutionThe cake was dissolved in MeOH
  7. filtrationfiltered
  8. customto remove residual solids
  9. additionThe filtrate was treated with charcoal
  10. temperaturewarmed to 40° C. for 2 h
  11. temperatureThe mixture was cooled to room temperature
  12. filtrationfiltered through a pad of Celite
  13. concentrationconcentrated
  14. additionThe residue was treated with isopropanol and heptane
  15. filtrationfiltered
  16. washwashed with MTBE

Sources & evidence

ORD record
ord-f36036b573b140b0b064f915ec2fcb8d
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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