Tributyltin Chloride → 2-(4-Tributylstannanyl-imidazol-1-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridine

HRID 1989255Notes

Reaction equation

HRID 1989255 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[N:8]=2)[CH:6]=1.C([Mg]Cl)(C)C.[Li+].[Cl-].[Sn:34](Cl)([CH2:43][CH2:44][CH2:45][CH3:46])([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:35][CH2:36][CH2:37][CH3:38]>C1COCC1>[CH2:43]([Sn:34]([CH2:35][CH2:36][CH2:37][CH3:38])([CH2:39][CH2:40][CH2:41][CH3:42])[C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[N:8]=2)[CH:6]=1)[CH2:44][CH2:45][CH3:46]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 433294Lithium ChlorideHCID 574687482-(4-Iodo-imidazol-1-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 574688332-(4-Tributylstannanyl-imidazol-1-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 2-(4-iodo-imidazol-1-yl)-4-trifluoromethyl-6-(4-trifluoromethylphenyl)-pyridine (example E.23) (4.83 g, 10 mmol) in THF (50 mL) at 0° C. was quickly added added i-PrMgCl.LiCl (1 M in THF, 11 mL, 11 mmol) and the mixture was stirred at 0° C. for 15 min. Then Bu3SnCl (3.25 mL, 12 mmol) was added, the cooling bath was removed and the mixture was stirred at 23° C. for 14 h. Poured into sat. NH4Cl-sol., extracted with EtOAc, washed with brine and dried over Na2SO4. Removal of the solvent in vacuum left a brown oil, which was purified by quick silica gel column chromatography with heptane/EtOAc 4:1 gave a yellow oil (4.42 g, 62%, ca. 90% pure). MS (ISP) 647.3 [(M+H)+].

Workup

  1. customthe cooling bath was removed
  2. additionPoured into sat. NH4Cl-sol
  3. extraction, extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent in vacuum
  7. waitleft a brown oil, which
  8. customwas purified by quick silica gel column chromatography with heptane/EtOAc 4:1
  9. customgave a yellow oil (4.42 g, 62%, ca. 90% pure)

Sources & evidence

ORD record
ord-6f62b395cce3429ca4defe058819114a
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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