Tributyltin Chloride → HCID 19879218, compound

HRID 1885596Notes

Reaction equation

HRID 1885596 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH2:15][CH2:14][CH2:13][N:11]3[CH:12]=2)=[CH:4][CH:3]=1.C([Li])CCC.[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]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH2:15][CH2:14][CH2:13][N:11]3[C:12]=2[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:6][CH:7]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 105696305H-Pyrrolo[1,2-a]imidazole, 2-(4-fluorophenyl)-6,7-dihydro-HCID 178418339Butyllithium

Product 1

HCID 19879218HCID 19879218, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

To a -78° C. solution of 2-(4-fluorophenyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole (2.0 g, 0.010 mole) in 60 ml of tetrahydrofuran (THF) is added 4.0 ml of 2.5M n-butyllithium. The solution is warmed to -30° C. for 20 minutes and then tributyltin chloride (3.3 g, 0.01 mole) in THF is added. The reaction is allowed to warm gradually to 20° C. and then is quenched with saturated ammonium chloride. Further workup and purification on silica as described in Example 6b yields the titled compound.

Workup

  1. temperatureto warm gradually to 20° C.
  2. customis quenched with saturated ammonium chloride
  3. customFurther workup and purification on silica

Sources & evidence

ORD record
ord-5dd3b3fc74764756879e59c5ed6e657c
Source dataset
uspto-grants-1992_09
Patent number
US05145858

Reaction notes

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