HCID 67377153, compound → HCID 52947473, compound

HRID 877454Notes

Reaction equation

HRID 877454 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][C:14]=1[Cl:15])[NH:11][C:10]1[C:9](=[O:16])[CH2:8][CH2:7][CH2:6][C:5]2=1.[CH3:17][Mg]Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][C:14]=1[Cl:15])[NH:11][C:10]1[C:9]([CH3:17])([OH:16])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

4

Reactant 2

HCID 67377153HCID 67377153, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 52947473HCID 52947473, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6,7-dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.1 g, 0.4 mmol) in anhydrous THF (5 mL) cooled to 0° C., MeMgCl (1.3 mL, 3.95 mmol, 3M in THF) was added dropwise. The reaction mixture was slowly warmed to room temperature and stirred for 5 h, cooled to 0° C., and then quenched with saturated NH4Cl (10 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and the solvent was removed under reduced pressure to give the crude material which was purified by column chromatography [EtOAc-hexane (1:9) as eluant] to give the title compound as a pale brown solid (0.01 g, 10%). 1H NMR (500 MHz. DMSO-d6, δ in ppm) 7.75 (s, 1H), 7.60 (s, 1H), 5.96 (s, 1H), 5.15 (s, 1H), 2.19-2.17 (m, 1H), 2.0-1.82 (m, 2H), 1.62-1.59 (m, 1H), 1.45 (s, 3H), 1.43-1.41 (m, 1H), 0.98-1.11 (m, 1H).

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with saturated NH4Cl (10 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. customthe solvent was removed under reduced pressure
  6. customto give the crude material which
  7. customwas purified by column chromatography [EtOAc-hexane (1:9) as eluant]

Sources & evidence

ORD record
ord-90ed6c35a7a8426198bb8569cb36718b
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

Loading…