Potassium Carbonate → HCID 69628639, compound

HRID 1743469Notes

Reaction equation

HRID 1743469 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([C:17]2[CH:18]=[C:19]([C:32]3[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=3)[C:20]([OH:31])=[C:21]([C:23]3[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=3)[CH:22]=2)=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH2:46]([O:48][C:49](=[O:54])[CH2:50][CH2:51][CH2:52]Br)[CH3:47]>CN(C=O)C>[CH2:46]([O:48][C:49](=[O:54])[CH2:50][CH2:51][CH2:52][O:31][C:20]1[C:21]([C:23]2[CH:24]=[C:25]([CH3:30])[CH:26]=[C:27]([CH3:29])[CH:28]=2)=[CH:22][C:17]([C:15](=[O:16])[NH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:18][C:19]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)[CH3:47]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 86583662HCID 86583662, compound

Product 1

HCID 69628639HCID 69628639, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2′-Hydroxy-3,5,3″,5″-tetramethyl-[1,1′:3′,1″]terphenyl-5′-carboxylic acid (7-phenyl-heptyl)-amide (180 mg, 0.327 mmol) in 2 mL DMF was added K2CO3 (24 mg, 0.174 mmol) and the reaction mixture was stirred for 10 min at room temperature. Then 4-bromobutyric acid ethyl ester (70 mg, 0.36 mmol) was added slowly to the reaction mixture. The reaction was stirred at room temperature for 2 d then it was heated for 45 min at a temperature between 40 and 50° C. Then it was worked up as in Step 1 of Example 146. 1H NMR (CDCl3) δ 1.18 (t, J=7.36 Hz, 3H); 1.27–1.37 (m, 6H); 1.44–1.64 (m, 6H); 1.95 (t, J=8.18 Hz, 2H); 2.54 (s, 12H); 2.57 (t, J=7.36 Hz, 2H); 3.25 (t, J=6, 54 Hz, 2H); 3.41 (quartet, J=7.36 Hz, 2H); 4.00 (quartet, J=8.18 Hz, 2H); 6.04 (m, 1H); 6.00–6.08 (m, 1H); 6.99 (s, 2H); 7.10–7.26 (m, 9H); 7.66 (s, 2H).

Workup

  1. stirringThe reaction was stirred at room temperature for 2 d
  2. temperatureit was heated for 45 min at a temperature between 40 and 50° C

Sources & evidence

ORD record
ord-e5294b16f6cf4c4ca083e81f509da416
Source dataset
uspto-grants-2006_03
Patent number
US07008636B2

Reaction notes

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