2-(Tri-n-butylstannyl)thiophene → HCID 66831870, compound

HRID 2190517Notes

Reaction equation

HRID 2190517 reaction equation
Br[C:2]1[C:10]2[C:6](=[N:7][N:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[N:9]=2)[C:5](Br)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:29]1[S:30][CH:31]=[CH:32][CH:33]=1)CCC>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:11]([N:8]1[N:9]=[C:10]2[C:2]([C:31]3[S:30][CH:29]=[CH:33][CH:32]=3)=[CH:3][CH:4]=[C:5]([C:29]3[S:30][CH:31]=[CH:32][CH:33]=3)[C:6]2=[N:7]1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 66831615HCID 66831615, compound

Product 1

HCID 66831870HCID 66831870, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4,7-Dibromo-2-dodecylbenzotriazole (100 mg, 0.224 mmol), and tributyl(thiophen-2-yl)stannane were dissolved in anhydrous THF (100 ml) and dichlorobis (triphenylphosphine)-palladium(II) (50 mg, 0.045 mmol) was added at room temperature. The mixture was refluxed for 12 hours under argon atmosphere. Solvent was evaporated under vacuum and the crude product was purified by column chromatography on silica gel to obtain 75 mg (74%) TBT. 1H NMR (400 MHz, CDCl3, δ): 8.01 (d, J=5.6 Hz, 2H), 7.52 (s, 2H), 7.28 (d, J=6.0 Hz, 2H), 7.09 (t, JA=8.8 Hz, JB=4.8, 2H), 4.60 (t, J=7.0 Hz, 2H), 2.10 (m, 2H), 1.38-1.15 (m, 18H), 0.80 (t, J=6.9 Hz, 3H); 13C NMR (100 MHz, DMSO-d6, δ): 142.4, 140.2, 128.4, 127.3, 125.8, 123.9, 123.0, 57.1, 32.2, 30.3, 29.9, 29.8, 29.7, 29.6, 29.5, 29.3, 26.9, 22.9, 14.4. MS (m/z): 451 [M+]

Workup

  1. temperatureThe mixture was refluxed for 12 hours under argon atmosphere
  2. customSolvent was evaporated under vacuum
  3. customthe crude product was purified by column chromatography on silica gel
  4. customto obtain 75 mg (74%) TBT

Sources & evidence

ORD record
ord-4f07c08dd9164f8b9e85a893b973197a
Source dataset
uspto-grants-2012_12
Patent number
US08324400B2

Reaction notes

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