Sodium Bicarbonate → HCID 69373266, compound

HRID 1861067Notes

Reaction equation

HRID 1861067 reaction equation
[C:1]1([C:7]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([CH:26]=[CH:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[N:14][N:15]3COCC[Si](C)(C)C)=[CH:11][CH:10]=2)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>C1COCC1>[C:1]1([C:7]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([CH:26]=[CH:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[N:14][NH:15]3)=[CH:11][CH:10]=2)=[CH2:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 69371688HCID 69371688, compound

Product 1

HCID 69373266HCID 69373266, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

6-(1-Phenyl-vinyl)-3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazole (16.2 mg, 0.0358 mmol) was dissolved in THF (0.6 mL) and was treated with tetrabutylammonium fluoride (TBAF, 1M in THF, 0.6 mL). The mixture was heated to 60° C. under argon for 4 h. The mix was cooled, neutralized with excess saturated sodium bicarbonate and the organic material was extracted into ethyl acetate and concentrated. This mix of 3 compounds (by TLC visualization) was treated with THF-water-TFA (1:1:2, 4 mL) for 30 min. The mix was diluted with toluene (20 mL), concentrated, neutralized with excess saturated sodium bicarbonate, and the organic material was extracted into ethyl acetate. The organic material was dried over sodium sulfate, decanted and concentrated. Purification by silica gel chromatography (2:8 ethyl acetate-hexane) gave 6-(1-Phenyl-vinyl)-3-styryl-1H-indazole (4.6 mg, 40%): Rf sm 0.62, p 0.24 (ethyl acetate-hexane 3:7); 1H NMR (300 MHz, CDCl3) δ 7.99 (d, 1H, J=8.5 Hz), 7.60-7.25 (m, 14H), 5.58 (d, 1H, J=1.1 Hz), 5.56 (d, 1H, J=1.1 Hz); HRMS (FAB) [m+H]/z Calc'd 323.1548, Found 323.1545.

Workup

  1. temperatureThe mix was cooled
  2. extractionthe organic material was extracted into ethyl acetate
  3. concentrationconcentrated
  4. additionThis mix of 3 compounds (by TLC visualization)
  5. additionwas treated with THF-water-TFA (1:1:2, 4 mL) for 30 min
  6. additionThe mix was diluted with toluene (20 mL)
  7. concentrationconcentrated
  8. extractionthe organic material was extracted into ethyl acetate
  9. dry with materialThe organic material was dried over sodium sulfate
  10. customdecanted
  11. concentrationconcentrated
  12. customPurification by silica gel chromatography (2:8 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-f41752d2d28647e9909def3b38d1e10d
Source dataset
uspto-grants-2003_03
Patent number
US06531491B1

Reaction notes

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