1,2-Dibromobenzene → 5-(2-bromo-phenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1499089Notes

Reaction equation

HRID 1499089 reaction equation
[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1Br.[O-]P([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O>CN(C=O)C.O.[Cu]I>[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:6]1[C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=2[C:4]2[CH2:3][N:2]([CH3:1])[CH2:15][CH2:14][C:5]1=2

Participants

8

Reactant 4

HCID 114141,2-DibromobenzeneHCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-

Product 1

HCID 673790385-(2-bromo-phenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (2 g, 9.986 mmol), 1,2-dibromobenzene (1.7 mL, 14.97 mmol), K3PO4 (6.35 g, 29.95 mmol), CuI (189 mg, 0.99 mmol) and L-proline (229 mg, 1.99 mmol) in dry DMF (20 mL) was stirred at 150° C. for 24 h. The reaction mixture was diluted with water (150 mL) and extracted with EtOAc (250 mL). The organic layer was washed with water (10×100 mL), dried over anhydrous sodium sulfate and evaporated to afford crude material, which was purified by column chromatography using neutral alumina and 3% EtOAc-hexane, to yield 5-(2-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole.

Workup

  1. extractionextracted with EtOAc (250 mL)
  2. washThe organic layer was washed with water (10×100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customto afford crude material, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-38f8a2d8a87648d69b236f38d1100867
Source dataset
uspto-grants-2015_12
Patent number
US09199985B2

Reaction notes

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