Sodium Carbonate → HCID 19078391, compound

HRID 964760Notes

Reaction equation

HRID 964760 reaction equation
[C:1]1(=[O:40])[N:5]([CH2:6][CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](OS(C(F)(F)F)(=O)=O)[CH:15]=3)[N:10]([S:25]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH:9]=2)[C:4](=[O:35])[C:3]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:2]12.[Cl-].[Li+].[S:43]1[CH:47]=[CH:46][CH:45]=[C:44]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[C:4]1(=[O:35])[N:5]([CH2:6][CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:44]4[S:43][CH:47]=[CH:46][CH:45]=4)[CH:15]=3)[N:10]([S:25]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH:9]=2)[C:1](=[O:40])[C:2]2=[CH:39][CH:38]=[CH:37][CH:36]=[C:3]12

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27339602-Thiopheneboronic acidHCID 19078399HCID 19078399, compound

Product 1

HCID 19078391HCID 19078391, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-(2-Phthalimidoethyl)-1-(p-toluenesulfonyl)-5-(trifluoromethanesulfonyloxy)-1H-indole (Example 11) (71 mg, 0.12 mmol) was dissolved in 1,2-dimethoxymethane (10 mL). Tetrakis(triphenylphosphine) palladium (14 mg, 0.012 mmol) and lithium chloride (10 mg, 0.24 mmol) were added and the resulting solution was stirred under argon at room temperature for 20 minutes. Thiophene-2-boronic acid (20 mg, 0.15 mmol) and sodium carbonate (2M solution in water, 0.1 ml) were added and the resulting mixture was stirred under argon at reflux for 4 hours. After cooling to room temperature, the crude product mixture was poured into ethyl acetate (20 mL), washed with water (20 mL), dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed on silica gel using hexane/ethyl acetate (4:1) as eluent to provide 3-(2-phthalimidoethyl)-1-(p-toluenesulfonyl)-5-(2-thienyl)-1H-indole (62 mg, 96%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ:-- 7.95 (d, J=8.9 Hz, 1H), 7.85-7.82 (A2 of A2B2 system, 2H), 7.80 (d, J=1.4 Hz, 1H), 7.73 (d, J=8.9 Hz, 2H), 7.72-7.69 (B2 of A2B2 system, 2H), 7.55 (dd, J=1.5 and 8.7 Hz, 1H), 7.46 (s, 1H), 7.29 (dd, J=1.2 and 3.5 Hz, 1H), 7.25 (dd, J=1.2 and 5.0 Hz, 1H), 7.19 (d, J=8.9 Hz, 2H), 7.07 (dd, J=3.5 and 5.0 Hz, 1H), 4.00 (t, J=7.4 Hz, 2H), 3.09 (t, J=7.4 Hz, 2H), 2.33 (s, 3H).

Workup

  1. stirringthe resulting mixture was stirred under argon
  2. temperatureat reflux for 4 hours
  3. temperatureAfter cooling to room temperature
  4. washwashed with water (20 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-6a37ba30ce574b45b9eaf66bc3eb3ac6
Source dataset
uspto-grants-1998_06
Patent number
US05770742

Reaction notes

Loading…