Potassium Carbonate → HCID 22611430, compound

HRID 1738136Notes

Reaction equation

HRID 1738136 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH2:16][CH2:15][CH:14]([NH2:22])[CH2:13][C:12]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:29][N:30]1[CH:34]=[C:33]([CH2:35][CH2:36]OS(C)(=O)=O)[CH:32]=[N:31]1>C(#N)C.CN(C)C1C=CN=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH2:16][CH2:15][CH:14]([NH:22][CH2:36][CH2:35][C:33]3[CH:32]=[N:31][N:30]([CH3:29])[CH:34]=3)[CH2:13][C:12]2=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15289310HCID 15289310, compoundHCID 226113086-benzyloxy-3-amino-1,2,3,4-tetrahydro-9H-carbazole

Product 1

HCID 22611430HCID 22611430, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.00 gm (3.422 mMol) 6-benzyloxy-3-amino-1,2,3,4-tetrahydro-9H-carbazole in 50 mL acetonitrile were added 1.04 gm (7.53 mMol) potassium carbonate followed by 1.26 gm (6.16 mMol) 2-(1-methyl-1H-pyrazol-4-yl)-1-mesyloxyethane and the reaction mixture was heated to reflux for 18 hours. To the reaction mixture were then added 0.021 gm (0.171 mMol) 4-dimethylaminopyridine and reflux was continued for 36 additional hours. The reaction mixture was cooled to room temperature and then partitioned between dichloromethane and water. The aqueous phase was extracted well with dichloromethane. All of the organic phases were combined, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 2.5% methanol in dichloromethane containing 0.5% ammonium hydroxide. Fractions shown to contain product were concentrated under reduced pressure to give 0.610 gm (44%) of the desired compound.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 18 hours
  3. temperaturereflux
  4. custompartitioned between dichloromethane and water
  5. extractionThe aqueous phase was extracted well with dichloromethane
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluting with 2.5% methanol in dichloromethane containing 0.5% ammonium hydroxide
  9. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-a34384bf97434628a8401b87e8c5636e
Source dataset
uspto-grants-1999_10
Patent number
US05962473

Reaction notes

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