Sodium Carbonate → 3-{6-[2-(2-Ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-5-(4-methyl-thiophen-3-yl)-benzoic Acid tert-butyl Ester

HRID 1670097Notes

Reaction equation

HRID 1670097 reaction equation
[C:1]([O:5][C:6](=[O:43])[C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:21]=2[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:10]=[C:9](Br)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH3:50][C:51]1[C:52](B(O)O)=[CH:53][S:54][CH:55]=1>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:43])[C:7]1[CH:8]=[C:9]([C:52]2[C:51]([CH3:50])=[CH:55][S:54][CH:53]=2)[CH:10]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:21]=2[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 50839314-Methyl-3-thiopheneboronic acidHCID 673397313-Bromo-5-{6-[2-(2-ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-benzoic Acid tert-butyl Ester

Product 1

HCID 673389343-{6-[2-(2-Ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-5-(4-methyl-thiophen-3-yl)-benzoic Acid tert-butyl EsterYield 88%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

3-Bromo-5-{6-[2-(2-ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-benzoic acid tert-butyl ester (2.0 g) was dissolved in 1,2-dimethoxyethane (40 mL), followed by addition of Pd(PPh3)4 (80 mg), 2 M solution of sodium carbonate (6 mL) and 4-methyl-3-thiopheneboronic acid (641 mg). The resulting reaction mixture was stirred at 85° C. for 2 h. After cooling the reaction mixture was filtered through Celite™, diluted with ethyl acetate and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified on a silica gel column using ethyl acetate and hexanes to the title compound (1.8 g, 88% yield).

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling the reaction mixture
  3. filtrationwas filtered through Celite™
  4. additiondiluted with ethyl acetate
  5. washwashed with water and brine
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. custompurified on a silica gel column

Sources & evidence

ORD record
ord-0e5b2314766048819fb39bdf3b9e406e
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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