HCID 13799191, compound → HCID 20155385, compound

HRID 2413718Notes

Reaction equation

HRID 2413718 reaction equation
[Br-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2-].[Na+].[CH2:24]([O:31][C:32]1[CH:44]=[CH:43][CH:42]=[C:41]2[C:33]=1[C:34]1[C:35]([CH2:57][O:58][CH3:59])=[C:36]([CH:55]=O)[N:37]=[CH:38][C:39]=1[N:40]2[S:45]([C:48]1[CH:54]=[CH:53][C:51]([CH3:52])=[CH:50][CH:49]=1)(=[O:47])=[O:46])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[CH2:24]([O:31][C:32]1[CH:44]=[CH:43][CH:42]=[C:41]2[C:33]=1[C:34]1[C:35]([CH2:57][O:58][CH3:59])=[C:36]([CH:55]=[CH2:2])[N:37]=[CH:38][C:39]=1[N:40]2[S:45]([C:48]1[CH:54]=[CH:53][C:51]([CH3:52])=[CH:50][CH:49]=1)(=[O:46])=[O:47])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 13799191HCID 13799191, compoundHCID 16212304Sodium;azanide;methyl(triphenyl)phosphanium;bromide

Product 1

HCID 20155385HCID 20155385, compoundYield 0%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g of methyltriphenylphosphoniumbromide+sodium amide (condition-ylide) in 8 ml of absolute tetrahydrofuran is stirred at room temperature under argon for 15 minutes. To it is added 500 mg of 5-benzyloxy-4-methoxymethyl-9-tosyl-beta-carboline-3-carbaldehyde and the reaction mixture is refluxed for 4 hours. After evaporation of the solvent, the residue is chromatographed over silica gel with cyclohexane/acetic acid=8+2 as eluant. 0.153 mg of 5-benzyloxy-4-methoxymethyl-9-tosyl-3-vinyl-beta-carboline with a melting point of 141°-143° C. is obtained.

Workup

  1. temperaturethe reaction mixture is refluxed for 4 hours
  2. customAfter evaporation of the solvent
  3. customthe residue is chromatographed over silica gel with cyclohexane/acetic acid=8+2 as eluant

Sources & evidence

ORD record
ord-e1e3a4da294b4a18adc377900c2157ba
Source dataset
uspto-grants-1988_01
Patent number
US04719210

Reaction notes

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