Sodium Carbonate → HCID 22247014, compound

HRID 890729Notes

Reaction equation

HRID 890729 reaction equation
[C:1]([O-])([O-])=[O:2].[Na+].[Na+].[CH:7]([C:9]1[S:13][C:12](B(O)O)=[CH:11][CH:10]=1)=O.IC1[CH:40]=[CH:39][C:21]([CH2:22][N:23]([S:35]([CH3:38])(=[O:37])=[O:36])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.CCO.CCOC(C)=O.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>[CH:1]([C:10]1[CH:11]=[CH:12][S:13][C:9]=1[C:7]1[CH:40]=[CH:39][C:21]([CH2:22][N:23]([S:35]([CH3:38])(=[O:37])=[O:36])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:20][CH:19]=1)=[O:2]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27734305-Formyl-2-thiopheneboronic acidHCID 22246725HCID 22246725, compound

Product 1

HCID 22247014HCID 22247014, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (91 mg, 0.08 mmol), Na2CO3 (0.87 mL, 1M) and 5-formyl-2-thiopheneboronic acid (247 mg, 1.58 mmol) were added to a solution of ethyl 7-{[4-iodobenzyl]-methanesulfonyl-amino}-heptanoate (371 mg, 0.79 mmol) in toluene (33 mL) and EtOH (6.5 mL). The reaction mixture was heated at reflux for 3 h. The solution was diluted with EtOAc and the organic solution was washed with water (2× followed by brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was purified via radial chromatography (25% EtOAc/hexanes to 50% EtOAc/hexanes) to afford the title compound of Step A (75 mg). 1H NMR (400 MHz, CDCl3) δ 9.89 (s, 1H), 7.44–7.60 (m, 5H), 7.21–7.31 (m, 1H), 4.45 (s, 2H), 4.10 (q, 2H), 3.20 (t, 2H), 2.90 (s, 3H), 2.25 (t, 3H), 1.58 (m, 4H), 1.35 (m, 7H); MS 452 (M+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. washthe organic solution was washed with water (2×
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified via radial chromatography (25% EtOAc/hexanes to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-987f0006112647a586f2ac4ee12892ad
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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