Dibutyltin dichloride → HCID 66619416, compound

HRID 417164Notes

Reaction equation

HRID 417164 reaction equation
C([Sn](Cl)(Cl)CCCC)CCC.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]([CH:24]([CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)[CH2:25]OCC3CCCCC3)[C:22]3[CH:40]=[C:41]([F:45])[C:42]([F:44])=[CH:43][C:21]=3[N:20]=2)=[CH:15][CH:14]=1.[NH2:46][C:47]1[CH:54]=[CH:53][C:50]([C:51]#[N:52])=[CH:49][CH:48]=1.C1([SiH3])C=CC=CC=1>O1CCCC1>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]([CH:24]([CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]3)[CH2:25][NH:46][C:47]3[CH:54]=[CH:53][C:50]([C:51]#[N:52])=[CH:49][CH:48]=3)[C:22]3[CH:40]=[C:41]([F:45])[C:42]([F:44])=[CH:43][C:21]=3[N:20]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 133964-AminobenzonitrileHCID 666192022-(4-Chloro-phenyl)-1-(1-cyclohexyl-2-cyclohexylmethoxy-ethyl)-5,6-difluoro-1H-benzoimidazole2×

Product 1

HCID 66619416HCID 66619416, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 7 mg (0.023 mmol) dibutyltin dichloride in 1 ml tetrahydrofuran were added 0.10 g (0.23 mmol) [2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetaldehyde (Example 143, intermediate c), 0.038 g (0.23 mMol) 4-aminobenzonitrile (commercially available) and 0.06 ml (0.46 mmol) phenylsilane (commercially available). The pale yellow solution was heated to 100° C. under microwave irradiation for 21 min. The light yellow solution was treated with silica gel and the suspension evaporated to dryness. The remaining solid was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane:ethyl acetate (100:0 to 70:30). The fractions containing the product were pooled and chromatographed a second time under the same conditions to give the title compound as a white solid (67%). MS (Turbo Spray): m/z=491.2 [M+H].

Workup

  1. additionThe light yellow solution was treated with silica gel
  2. customthe suspension evaporated to dryness
  3. customThe remaining solid was purified by silica gel chromatography
  4. washeluting with a gradient of heptane:ethyl acetate (100:0 to 70:30)
  5. additionThe fractions containing the product
  6. customchromatographed a second time under the same conditions

Sources & evidence

ORD record
ord-985639761e9d429da4df0e29d8641a16
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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