3-Fluorobenzyl chloride → HCID 13392778, compound

HRID 329963Notes

Reaction equation

HRID 329963 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([OH:22])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[F:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33]Cl>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([O:22][CH2:33][C:32]1[CH:35]=[CH:36][CH:37]=[C:30]([F:29])[CH:31]=1)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 99743-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 178470225HCID 178470225, compound

Product 1

HCID 13392778HCID 13392778, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, 0.3 g of 5-hydroxy-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester is refluxed for 4 hours in 60 ml of ethanol with 0.3 g of potassium carbonate and 0.174 g of 3-fluorobenzyl chloride. After filtration and concentration under vacuum, the residue is chromatographed over silica gel (methylene chloride +ethanol/1000+25), thus obtaining 0.167 g of 5-(3-fluorobenzyloxy)-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester, mp 188.0° C.

Workup

  1. filtrationAfter filtration and concentration under vacuum
  2. customthe residue is chromatographed over silica gel (methylene chloride +ethanol/1000+25)

Sources & evidence

ORD record
ord-6c6a823a2f7b44eb8c76810b6fc91ec4
Source dataset
uspto-grants-1990_01
Patent number
US04894377

Reaction notes

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