Potassium Carbonate → HCID 59380348, compound

HRID 2353249Notes

Reaction equation

HRID 2353249 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.[S:27]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)C>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][C:22]([C:29]4[CH:30]=[CH:31][S:27][CH:28]=4)=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 581760Thiophene-3-boronic acidHCID 68426737HCID 68426737, compound

Product 1

HCID 59380348HCID 59380348, compoundYield 35.5%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of the compound from step 1 (140 mg, 0.3 mmol), thiophene-3-boronic acid (70 mg, 055 mmol), palladium(II) acetate (20 mg, 0.09 mmol) and triphenyl phosphine (40 mg, 0.18 mmol) in DME (5 mL) was added potassium carbonate (140 mg, 1 mmol), ethanol (0.5 mL) and water (0.5 mL). The mixture was stir at rt under Ar for 30 min and then was heated to 80° C. for 16 h. After cooling to rt temperature, the mixture was poured onto 20 mL ice-water, followed by extraction with EtOAc (3×10 mL). The combined organic layers were washed with water (2×10 mL), brine (10 mL) and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to obtain the crude product, which was purified by silica gel flash chromatography (1% MeOH in CH2Cl2) to afford the title product (45 mg, 35%): MS (ESI) m/z 423 (M+H); 1H NMR (400 MHz, CDCl3) δ 2.56 (t, J=7.2 Hz, 2H), 2.64 (t, J=4.8 Hz, 4H), 2.77 (t, J=7.2 Hz, 2H), 3.16 (t, J=4.8 Hz, 4H), 3.70 (s, 3H), 6.90-6.99 (m, 6H), 7.34-7.37 (m, 3H), 7.51 (m, 2H).

Workup

  1. temperaturewas heated to 80° C. for 16 h
  2. temperatureAfter cooling to rt temperature
  3. extractionfollowed by extraction with EtOAc (3×10 mL)
  4. washThe combined organic layers were washed with water (2×10 mL), brine (10 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customto obtain the crude product, which
  8. customwas purified by silica gel flash chromatography (1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-10ac90f13a664a04b76ce881b3657a61
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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