2-(Dimethylamino)ethanol → tert-butyl 6-(2-(dimethylamino)ethoxy)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 1677041Notes

Reaction equation

HRID 1677041 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:21][CH2:20][C:11]2[NH:12][C:13]3[C:14](I)=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][OH:34]>C(Cl)Cl.[Cu]I>[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][O:34][C:14]1[C:13]2[NH:12][C:11]3[CH2:20][CH2:21][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][C:10]=3[C:18]=2[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 62657Potassium Phosphate, TribasicHCID 21952696tert-Butyl-6-iodo-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 57541297tert-butyl 6-(2-(dimethylamino)ethoxy)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylateYield 67.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

tert-Butyl-6-iodo-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (500 mg, 1.26 mmol), copper(I) iodide (71.7 mg, 0.38 mmol) and tri-potassium orthophosphate (533 mg, 2.51 mmol) were suspended in 2-dimethylaminoethanol (10 ml, 99.40 mmol) and sealed into a microwave tube. The reaction was heated to 150° C. for 1 hour in the microwave reactor and cooled to RT. The reaction mixture was diluted with DCM (100 mL), and washed with 2N NaOH (3×50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was purified by preparative HPLC (0.1% NH3, CH3CN/H2O gradient) to afford tert-butyl 6-(2-(dimethylamino)ethoxy)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (304 mg, 67%) as a yellow gum.

Workup

  1. customsealed into a microwave tube
  2. temperaturecooled to RT
  3. washwashed with 2N NaOH (3×50 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto afford crude product
  8. customThe crude product was purified by preparative HPLC (0.1% NH3, CH3CN/H2O gradient)

Sources & evidence

ORD record
ord-75554dbd2f68405a9fb45e0a5a27fc9d
Source dataset
uspto-grants-2011_08
Patent number
US08008279B2

Reaction notes

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