Tributyltin Chloride → HCID 67347378, compound

HRID 1676283Notes

Reaction equation

HRID 1676283 reaction equation
Br[C:2]1[O:6][C:5]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.[CH2:20]([Sn:24]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:26][CH2:27][CH2:28][CH3:29])Cl)[CH2:21][CH2:22][CH3:23]>C1COCC1>[CH3:14][N:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:5]2[O:6][C:2]([Sn:24]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:20][CH2:21][CH2:22][CH3:23])=[CH:3][CH:4]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 2838208HCID 2838208, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 67347378HCID 67347378, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A round-bottomed flask was charged with 1-((5-bromofuran-2-yl)methyl)-4-methylpiperazine (1.29 g, 4.88 mmol), and THF (20 mL). The solution was cooled to −78° C. in a dry ice/acetone bath. tert-Butyllithium (6.56 mL, 10.5 mmol; 1.6 M in pentane) was added, and the reaction mixture was stirred for 30 minutes. Tributylchlorostannane (1.12 mL, 4.15 mmol) was added the reaction mixture was stirred for 30 minutes. The reaction mixture was quenched by adding pH 7 phosphate buffer (20 mL) and warming to room temperature. The reaction mixture was extracted with EtOAc (50 mL), washed with brine (2×50 mL), dried over sodium sulfate, filter and concentrate. Purify by Biotage 40S (EtOAc). Isolated product (1.20 g, 52%) as a green oil. 1H NMR (CDCl3, 400 MHz) δ 6.47 (d, J=3.1 Hz, 1H), 6.21 (d, J=2.3 Hz, 1H), 3.62 (s, 2H), 2.50 (br s, 8H), 2.27 (s, 3H), 1.53 (m, 6H), 1.33 (m, 6H), 1.06 (m, 6H), 0.88 (m, 9H).

Workup

  1. stirringwas stirred for 30 minutes
  2. customThe reaction mixture was quenched
  3. additionby adding pH 7 phosphate buffer (20 mL)
  4. temperaturewarming to room temperature
  5. extractionThe reaction mixture was extracted with EtOAc (50 mL)
  6. washwashed with brine (2×50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfilter
  9. concentrationconcentrate
  10. customPurify by Biotage 40S (EtOAc)

Sources & evidence

ORD record
ord-d7e4fba364e64c8691716f474b7f1495
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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