Potassium Carbonate → 7-(9H-carbazol-2-yloxy)-heptanoic acid benzyloxyamide

HRID 1636072Notes

Reaction equation

HRID 1636072 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:19][C:20]1[CH:32]=[CH:31][C:30]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][C:22]=2[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:8][NH:9][C:10](=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:19][C:20]1[CH:32]=[CH:31][C:30]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][C:22]=2[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 935512-HydroxycarbazoleHCID 865865457-Bromo-heptanoic acid benzyloxyamide

Product 1

HCID 865865467-(9H-carbazol-2-yloxy)-heptanoic acid benzyloxyamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner analogous to that of example 1 (b), 7-bromo-heptanoic acid benzyloxy-amide (1.8 g, 5.7 mmol) was reacted with 2-hydroxycarbazole (1.05 g, 5.7 mmol) in the presence of potassium carbonate (1.2 g, 8.6 mmol) in dimethyl formamide to give 7-(9H-carbazol-2-yloxy)-heptanoic acid benzyloxyamide as an almost colorless wax (yield 0.53 g, 22%; purified by column chromatography using silica gel and ethyl acetate: heptane 4:6 to 6:4 as an eluent). MS (M−H+)=415.

Sources & evidence

ORD record
ord-e398d13af0fd45b5a26b968db285ed07
Source dataset
uspto-grants-2003_01
Patent number
US06512123B2

Reaction notes

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