Potassium Carbonate → 8-(9H-carbazol-2-yloxy)-octanoic acid benzyloxyamide

HRID 1636067Notes

Reaction equation

HRID 1636067 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:20][C:21]1[CH:33]=[CH:32][C:31]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][C:23]=2[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][NH:9][C:10](=[O:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:20][C:21]1[CH:33]=[CH:32][C:31]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][C:23]=2[CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 935512-HydroxycarbazoleHCID 113364038-Bromo-octanoic acid benzyloxyamide

Product 1

HCID 865865438-(9H-carbazol-2-yloxy)-octanoic acid benzyloxyamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner analogous to that of example 1(b), 8-bromo-octanoic acid benzyloxy-amide (example 1(a); 0.3 g, 1.1 mmol) was reacted with 2-hydroxy-9H-carbazol (0.3 g, 1.1 mmol) in the presence of potassium carbonate (0.15 g, 1.1 mmol) and DMF as solvent to give 8-(9H-carbazol-2-yloxy)-octanoic acid benzyloxyamide as an almost colorless wax (yield 0.1 g, 20%; purified by column chromatography using silica gel and ethyl acetate as eluent). MS (M+H+)=483.

Sources & evidence

ORD record
ord-e6019aabb1ff4ab5a8b12c881e871626
Source dataset
uspto-grants-2003_01
Patent number
US06512123B2

Reaction notes

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