Tetrahydrofuran → 2-Fluoro-3-(tributylstannyl)pyridine

HRID 580813Notes

Reaction equation

HRID 580813 reaction equation
C([N-]C(C)C)(C)C.[Li+].O1CCCC1.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.[CH2:21]([Sn:25](Cl)([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH3:24]>CCCCCC>[F:14][C:15]1[C:20]([Sn:25]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:21][CH2:22][CH2:23][CH3:24])=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 97462-FluoropyridineHCID 15096Tributyltin ChlorideHCID 2724682Lithium diisopropylamide

Product 1

HCID 110903192-Fluoro-3-(tributylstannyl)pyridine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

To a mixture of lithium diisopropylamide (1.5M in cyclohexane, 43 mL) and tetrahydrofuran (60 mL) cooled to -70° C. was added 2-fluoropyridine (6.0 mL) at such a rate that the temperature remained below -70° C. After 1.5 hours, tributyltin chloride (15 mL) was added, and the mixture was allowed to warm to room temperature. The mixture was diluted with hexane, washed with water, dried, filtered, and evaporated. Chromatography of the residue over silica gel (cyclohexane/ethyl acetate 98/2) gave 2-fluoro-3-tributylstannylpyridine (17 g).

Workup

  1. customremained below -70° C
  2. temperatureto warm to room temperature
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-5cfea6c7f3bd42c9bd827256cd5c91b3
Source dataset
uspto-grants-1999_07
Patent number
US05919779

Reaction notes

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