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

HRID 1927979Notes

Reaction equation

HRID 1927979 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH:10]=[C:9]([C:23]([F:26])([F:25])[F:24])[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]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH:10]=[C:9]([C:23]([F:26])([F:25])[F:24])[N:8]=2)[CH:6]=1)[CH2:44][CH2:45][CH3:46]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 433294Lithium ChlorideHCID 574688062-(4-Iodo-imidazol-1-yl)-6-trifluoromethyl-4-(4-trifluoromethyl-phenyl)-pyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 574688342-(4-Tributylstannanyl-imidazol-1-yl)-6-trifluoromethyl-4-(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)-6-trifluoromethyl-4-(4-trifluoromethyl-phenyl)-pyridine (example E.93) (1.2 g, 2.48 mmol) in THF (15 mL) at 0° C. was quickly added added i-PrMgCl.LiCl (1 M in THF, 3.0 mL, 3.0 mmol) and the mixture was stirred at 0° C. for 15 min. Then Bu3SnCl (0.94 mL, 3.48 mmol) was added, the cooling bath was removed and the mixture was stirred at 23° C. for 48 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 alox (neutral) column chromatography with heptane/methylene chloride gave a yellow oil (1.7 g, 106%, ca. 90% pure). MS (ISP) 648.3 [(M+H)+].

Workup

  1. customat 0° C.
  2. customthe cooling bath was removed
  3. additionPoured into sat. NH4Cl-sol
  4. extraction, extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent in vacuum
  8. waitleft a brown oil, which
  9. customwas purified by alox (neutral) column chromatography with heptane/methylene chloride
  10. customgave a yellow oil (1.7 g, 106%, ca. 90% pure)

Sources & evidence

ORD record
ord-bae38a320752401b8e3b2380a11b9fba
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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