Triethylamine → methyl 4-oxo-2,3,4,9-tetrahydro-1H-carbazole-5-carboxylate

HRID 1775197Notes

Reaction equation

HRID 1775197 reaction equation
Br[C:2]1[C:11]([NH:12][C:13]2[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH:14]=2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C(Cl)Cl.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:19]=[C:15]1[C:14]2[C:2]3[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[CH:10][C:11]=3[NH:12][C:13]=2[CH2:18][CH2:17][CH2:16]1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 223377243-(3-Carbomethoxy-2-bromoanilino)cyclohex-2-en-1-one

Product 1

HCID 11368514methyl 4-oxo-2,3,4,9-tetrahydro-1H-carbazole-5-carboxylate

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 2-bromo-3-(3-oxocyclohex-1-enylamino)benzoate (0.97 g, 3.0 mmol), palladium acetate (0.14 g, 0.6 mmol), tri-o-tolylphosphine (0.73 g, 2.4 mmol), and triethylamine (0.38 g, 3.6 mmol) in acetonitrile (10 mL) was heated in a sealed tubule flushed with nitrogen at 100° C. for 20 h. The cooled reaction mixture was diluted with DCM (3×50 mL) and water (10 mL). The organic layer was separated, washed with water, dried (Na2SO4), and concentrated.

Workup

  1. temperaturewas heated in a sealed
  2. customtubule flushed with nitrogen at 100° C. for 20 h
  3. customThe cooled reaction mixture
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e024770b8e804559b7e844b1ccac61bd
Source dataset
uspto-grants-2016_02
Patent number
US09260440B2

Reaction notes

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