Tetrahydrofuran → HCID 22914783, compound

HRID 1377571Notes

Reaction equation

HRID 1377571 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=O)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:17]=1.[CH2:18]1[CH2:22]O[CH2:20][CH2:19]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:17]=1)[CH2:7][CH2:8][C:9]1[C:10](/[C:15]/2=[C:19]2/[CH2:20][CH:10]([CH3:9])[NH:11][CH2:12][CH:18]/2[CH3:22])=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 98162608-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one

Product 1

HCID 22914783HCID 22914783, compoundYield 53%

Procedure

To a cooled (ice-bath), stirred solution of 8-chloro-5,6-dihydro-11 H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (6.3 g, 26 mmol) in THF (50 mL) was added the above Grignard reagent. The reaction was allowed to stir for 1 hr. at this temperature and then quenched with NH4Cl solution. The product was extracted 3× with EtOAc, washed once with brine, dried (Na2SO4), filtered and solvent removed to give a crude brown material which was chromatographed to give the title compound (5.1 g, 53% yield) as a yellowish glass.

Workup

  1. temperatureTo a cooled (ice-bath)
  2. customat this temperature and then quenched with NH4Cl solution
  3. extractionThe product was extracted 3× with EtOAc
  4. washwashed once with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customsolvent removed
  8. customto give a crude brown material which
  9. customwas chromatographed

Sources & evidence

ORD record
ord-73cda9dbb64f4f5bb151026871775597
Source dataset
uspto-grants-1997_09
Patent number
US05665726

Reaction notes

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