Sodium Carbonate → HCID 16110520, compound

HRID 2235881Notes

Reaction equation

HRID 2235881 reaction equation
[S:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.I[C:10]1[CH:35]=[CH:34][C:13]([O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[C@H:24]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:23][CH2:22]3)=[CH:12][CH:11]=1.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[S:1]1[CH:5]=[CH:4][C:3]([C:10]2[CH:35]=[CH:34][C:13]([O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C@H:24]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:23][CH2:22]4)=[CH:12][CH:11]=2)=[CH:2]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 581760Thiophene-3-boronic acidHCID 16110430HCID 16110430, compound

Product 1

HCID 16110520HCID 16110520, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of thiophene-3-boronic acid (53 mg, 0.42 mmol), ethyl {(1 S)-5-[3-(4-iodophenoxy)propoxy]-2,3-dihydro-1H-inden-1-yl}acetate (50 mg, 0.10 mmol, Example 94) in toluene (1.8 mL), and 1,4-dioxane (0.45 mL), was added PdCl2(dppf)-CH2Cl2 (7.6 mg, 0.01 mmol), and argon was passed through the mixture for 30 min. Then Na2CO3 (2 N aqueous solution, 0.50 mL) was added, and the mixture was heated to 75° C. for 48 h. The reaction was cooled to rt, and extracted with EtOAc (2×). The combined organic phases were washed with NaHCO3 (saturated aqueous solution), dried, filtered and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel to give 33 mg (73%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.51 (d, 2H), 7.40-7.31 (m, 3H), 7.06 (d, 1H), 6.97 (d, 2H), 6.80 (s, 1H), 6.72 (dd, 1H), 4.24-4.10 (m, 6H), 3.60-3.48 (m, 1H), 2.98-2.90 (m, 2H), 2.72 (dd, 1H), 2.46-2.36 (m, 2H), 2.36-2.23 (m, 2H), 1.85-1.70 (m, 1H), 1.30 (t, 3H).

Workup

  1. temperatureThe reaction was cooled to rt
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic phases were washed with NaHCO3 (saturated aqueous solution)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by preparative thin layer chromatography on silica gel

Sources & evidence

ORD record
ord-556e29e458344721baeeb0ed9d325d20
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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