Tributyltin Chloride → HCID 57468836, compound

HRID 1927980Notes

Reaction equation

HRID 1927980 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]=[C:10]([N:18]3[CH:22]=[C:21](I)[N:20]=[CH:19]3)[N:9]=2)=[CH:4][CH:3]=1.[Cl-].[Li+].C([Mg]Cl)(C)C.[CH2:31]([Sn:35](Cl)([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH3:34].[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]=[C:10]([N:18]3[CH:22]=[C:21]([Sn:35]([CH2:36][CH2:37][CH2:38][CH3:39])([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:31][CH2:32][CH2:33][CH3:34])[N:20]=[CH:19]3)[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 57468793HCID 57468793, compoundHCID 178461733HCID 178461733, compound

Product 1

HCID 57468836HCID 57468836, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-(4-fluoro-phenyl)-2-(4-iodo-imidazol-1-yl)-6-trifluoromethyl-pyrimidine (Example E.79) (0.87 g, 2.0 mmol) in THF (14 ml) was added at 0° C. isopropyl-magnesium chloride lithium chloride (1M in THF, 2.44 ml, 2.44 mmol). The reaction mixture was allowed to stir for 15 min at 0° C., tributyltin chloride (0.87 g, 2.67 mmol) was added, the reaction mixture was stirred at room temperature for 16 h, poured into saturated ammonium chloride solution (30 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with brine (30 ml), dried (MgSO4) and evaporated. The crude product was further purified by flash chromatography on silica gel (ethylacetate/heptane) to yield the title compound (0.69 g, 58%) as a light yellow oil. MS (ISP) 598.7 [(M+H)+].

Workup

  1. customwas added at 0° C.
  2. stirringthe reaction mixture was stirred at room temperature for 16 h
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. washThe combined organic layers were washed with brine (30 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was further purified by flash chromatography on silica gel (ethylacetate/heptane)

Sources & evidence

ORD record
ord-b410c3f4314c44cbb5b9049c755ad527
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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