Potassium Carbonate → HCID 86583672, compound

HRID 1884762Notes

Reaction equation

HRID 1884762 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:47])[C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[C:20]([O:33][CH2:34][CH2:35]Br)=[C:19]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[CH:38]=3)[CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[OH:54][C:55]1[CH:64]=[C:63]([OH:65])[CH:62]=[CH:61][C:56]=1[C:57]([O:59][CH3:60])=[O:58]>CC(C)=O>[CH3:60][O:59][C:57](=[O:58])[C:56]1[CH:61]=[CH:62][C:63]([O:65][CH2:35][CH2:34][O:33][C:20]2[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)=[CH:22][C:17]([C:16](=[O:47])[NH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:18][C:19]=2[C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[CH:38]=2)=[CH:64][C:55]=1[OH:54]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16523Methyl 2,4-DihydroxybenzoateHCID 22237605HCID 22237605, compound

Product 1

HCID 86583672HCID 86583672, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N-(8-phenyl octyl)-4-(2-bromo-ethoxy)-3,5-bis(m-trifluoromethylphenyl) benzamide (1.48 g, 2.05 mmol, 1 eq) in acetone (21 mL) was added K2CO3 (1.42 g, 10.25 mmol, 5eq) and methyl 2,4-dihydroxybenzoate (0.340 g, 2.05 mmol, 1.0 eq). The reaction was heated at reflux for overnight, cooled to rt and concentrated in vacuo. The residue was partitioned between EtOAc and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (30% EtOAc:hexane) to afford 2-hydroxy-4-{2-[5′-(8-phenyl-octylcarbamoyl)-3,3″-bis-trifluoromethyl-[1,1′:3′,1″]terphenyl-2′-yloxy]-ethoxy}-benzoic acid methyl ester (0.98 g, 60%) as a colorless oil. 1H NMR (CDCl3) δ 10.90 (s, 1H); 7.92-7.78 (m, 7H); 7.66-7.50 (m, 4H); 7.27-7.12 (m, 5H); 6.18-6.10 (m, 3H); 3.92 (s, 3H); 3.66-3.40 (m, 6H); 2.58 (t, 2H); 1.60 (m, 4H); 1.28 (m, 8H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for overnight
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between EtOAc and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (30% EtOAc:hexane)

Sources & evidence

ORD record
ord-ed1cfc02cd9b419d87150ac8f61411f7
Source dataset
uspto-grants-2004_07
Patent number
US06765021B2

Reaction notes

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