3-Methoxypropyne → 6-Chloro-5-(4-chlorobenzyl)-4-methoxymethyl-3-(5-methoxymethylisoxazol-3-yl)-beta-carboline

HRID 1720331Notes

Reaction equation

HRID 1720331 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:8]=2[C:9]2[C:10]([CH2:23][O:24][CH3:25])=[C:11]([CH:20]=[N:21][OH:22])[N:12]=[CH:13][C:14]=2[NH:15]3)=[CH:4][CH:3]=1.[Cl:28][O-].[Na+].[CH3:31][O:32][CH2:33][C:34]#[CH:35]>O1CCCC1.C(OCC)(=O)C>[Cl:28][C:19]1[C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:27][CH:26]=2)=[C:8]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]1[CH:13]=[N:12][C:11]([C:20]3[CH:35]=[C:34]([CH2:33][O:32][CH3:31])[O:22][N:21]=3)=[C:10]([CH2:23][O:24][CH3:25])[C:9]2=1

Participants

6

Reactant 3

HCID 693933-MethoxypropyneHCID 23665760Sodium HypochloriteHCID 1363755785-(4-Chlorobenzyl)-4-methoxymethyl-beta-carboline-3-carbaldehyde-oxime

Product 1

HCID 224177716-Chloro-5-(4-chlorobenzyl)-4-methoxymethyl-3-(5-methoxymethylisoxazol-3-yl)-beta-carbolineYield 5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.5 g (0.0013 mol) 5-(4-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carbaldehyde-oxime is suspended in 25 ml of tetrahydrofuran and mixed with 5 ml of sodium hypochlorite solution under protective gas (argon). After 20 minutes no more initial material can be detected by thin-layer chromatography. 0.7 ml of methylpropargylether is instilled over 2.5 hours then the mixture is stirred for another hour. After it is left standing overnight it is diluted with ethyl acetate, washed neutral with water, dried and concentrated by evaporation. From the evaporation residue 0.031 g (5% of theory) of 6-chloro-5-(4-chlorobenzyl)-4-methoxymethyl-3-(5-methoxymethylisoxazol-3-yl)-β-carboline, melting point 198°-200° C., is obtained by chromatography on silica gel and recrystallization from ethanol/ether.

Workup

  1. waitAfter it is left
  2. waitstanding overnight
  3. washwashed neutral with water
  4. customdried
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2c7512aa5e964038a0f58e5b57cf5210
Source dataset
uspto-grants-1996_04
Patent number
US05506234

Reaction notes

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