5-((Z)-2-(4-fluorophenyl)prop-1-enyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole → 5-(2-(4-fluorophenyl)propyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole

HRID 509875Notes

Reaction equation

HRID 509875 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH3:25])=[CH:9]\[N:10]2[C:18]3[CH:17]=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[C:12]3[CH2:20][N:21]([CH3:24])[CH2:22][CH2:23][C:11]2=3)=[CH:4][CH:3]=1.FC1C=CC(C(=C)CN2C3C=CC(C)=CC=3C3CN(C)CCC2=3)=CC=1>CO.C(O)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:25])[CH2:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[C:12]3[CH2:20][N:21]([CH3:24])[CH2:22][CH2:23][C:11]2=3)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 461995815-((Z)-2-(4-fluorophenyl)prop-1-enyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indoleHCID 594548975-(2-(4-fluorophenyl)allyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole

Product 1

HCID 578759635-(2-(4-fluorophenyl)propyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

A mixture of compound 5-((Z)-2-(4-fluorophenyl)prop-1-enyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole and 5-(2-(4-fluorophenyl)allyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole (of ratio 1:3, 1.8 g, 5.38 mmol, 1 equiv) were shaken in a 250 ml Parr Shaker vessel with 180 mg of Pd/C in 50 ml of Methanol/acetic acid (10:1) mixture for 18 hours under 60 psi H2. It was filtered over a celite bed with methanol and evaporated under vacuum. The residue was diluted with ethyl acetate (500 ml) and washed with 50 ml of satd. sodium bicarbonate solution and then brine. The organic part was concentrated under reduced pressure and column purified over 100-200 silica gel using 0 to 50% ethyl acetate in hexanes as eluant, at an interval of 5%. Yield: 685 mg (38%).

Workup

  1. filtrationIt was filtered over a celite bed with methanol
  2. customevaporated under vacuum
  3. additionThe residue was diluted with ethyl acetate (500 ml)
  4. washwashed with 50 ml of satd
  5. concentrationThe organic part was concentrated under reduced pressure and column
  6. custompurified over 100-200 silica gel using 0 to 50% ethyl acetate in hexanes as eluant, at an interval of 5%

Sources & evidence

ORD record
ord-cec98bebb0614f1b99f7535dad8aea57
Source dataset
uspto-grants-2015_08
Patent number
US09096591B2

Reaction notes

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