Potassium Carbonate → HCID 86583672, compound

HRID 1743519Notes

Reaction equation

HRID 1743519 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-phenyloctyl)-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, 5 eq) 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-c5c604c0dd034d73b2a1d3af2cd28b60
Source dataset
uspto-grants-2006_03
Patent number
US07008636B2

Reaction notes

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