Tributylstannane → HCID 90073294, compound

HRID 576387Notes

Reaction equation

HRID 576387 reaction equation
C(OC1C(Br)=[C:7]([C@H:21]2[C@H:26]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@@H:25]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@H:24]([O:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C@@H:23]([CH2:51][O:52][CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[O:22]2)[CH:8]=[C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)[C:10]=1[Cl:11])C=C.[CH3:61]CCC[SnH](CCCC)CCCC.CC(N=NC(C#N)(C)C)(C#N)C.[F-].[K+].[CH3:88][CH2:89][O:90][C:91]([CH3:93])=O>>[Cl:11][C:10]1[C:91]2[O:90][CH2:89][CH:88]([CH3:61])[C:93]=2[C:7]([C@H:21]2[C@H:26]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C@@H:25]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@H:24]([O:43][CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[C@@H:23]([CH2:51][O:52][CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[O:22]2)=[CH:8][C:9]=1[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=1

Participants

6

Reactant 5

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 8857Ethyl AcetateHCID 522689Potassium FluorideHCID 90073524HCID 90073524, compound

Product 1

HCID 90073294HCID 90073294, compoundYield 40%

Conditions

Temperature
120 °C

Procedure

To a solution of the 163 (1.52 g, 1.71 mmol) were added Bu3SnH (3.7 ml, 13.7 mmol) and AIBN (112 mg, 0.68 mmol). After stirring for 20 h at 120° C., aq. 10% KF solution was added to quench the reaction. The residue was dissolved in EtOAc (100 mL), washed with saturated NaHCO3 solution, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the compound 164 (538 mg, 40%).

Workup

  1. customto quench
  2. customthe reaction
  3. washwashed with saturated NaHCO3 solution
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-72070b4c111f483b9bbc897408a5f064
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

Loading…