2-(Tri-n-butylstannyl)thiophene → HCID 19078318, compound

HRID 964839Notes

Reaction equation

HRID 964839 reaction equation
Br[C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([C:35]4[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=4)=[CH:10][C:11]=3[C:12]2([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:46]1[S:47][CH:48]=[CH:49][CH:50]=1)CCC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCCCCC.C1COCC1>[CH2:25]([C:12]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:11]2[CH:10]=[C:9]([C:35]3[CH:36]=[CH:37][N:38]=[CH:39][CH:40]=3)[CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:14][C:2]([C:46]1[S:47][CH:48]=[CH:49][CH:50]=1)=[CH:3][CH:4]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 19078316HCID 19078316, compound

Product 1

HCID 19078318HCID 19078318, compoundYield 72.38%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21883165Tetrahydrofuran hexaneSolvent

Procedure

4-(7-bromo-9,9-didecyl-9H-2-fluorenyl)pyridine (2.32 g, 3.85 mmol) was weighed directly into a single-necked round bottom flask equipped with a magnetic stirrer and condenser which had been dried in an oven at 130° C. overnight. Toluene (20 ml, dried over CaCl2 and freshly distilled) and 2-(tributylstannyl)thiophene (1.47 ml 4.62 mmol) were added to the flask and the solution was degassed with nitrogen for 15 min. Tetrakis(triphenylphosphine)palladium (0) (0.34 g, 0.29 mmol) was added and the solution was heated at reflux for 16 hr under nitrogen. The reaction was cooled to room temperature and the toluene was removed under reduced pressure. The product was isolated by column chromatography using silica gel and 90:10 hexane/THF as the eluent to afford a yellow oil in 72.38% yield. If the oil was allowed to stand at room temperature it slowly solidified into a pale yellow waxy solid mp 58° C.-61° C. Mass Spec. m/z 605, (M+), 464, (M-C10 H21). Elemental Analysis: Calculated for C42H55NS: C, 83.25; H, 9.15; N, 2.31. Found: C, 83.34; H, 8.89; N, 2.31.

Workup

  1. customequipped with a magnetic stirrer and condenser which
  2. customhad been dried in an oven at 130° C. overnight
  3. dry with materialToluene (20 ml, dried over CaCl2
  4. additionwere added to the flask
  5. customthe solution was degassed with nitrogen for 15 min
  6. temperaturethe solution was heated
  7. temperatureat reflux for 16 hr under nitrogen
  8. customthe toluene was removed under reduced pressure
  9. customThe product was isolated by column chromatography
  10. customto afford a yellow oil in 72.38% yield
  11. customto stand at room temperature

Sources & evidence

ORD record
ord-a6de475bd341442f80500dd995ad7a39
Source dataset
uspto-grants-1998_06
Patent number
US05770737

Reaction notes

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