Tetramethyltin → HCID 20781242, compound

HRID 2181273Notes

Reaction equation

HRID 2181273 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:35])=[C:6]([C:8]2([S:22]([C:25]3[CH:26]=[N:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=3)(=[O:24])=[O:23])[CH2:13][CH2:12][CH:11]([NH:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])[CH2:10][CH2:9]2)[CH:7]=1.[F-].[Cs+].[C:38](P(C(C)(C)C)C(C)(C)C)(C)(C)C.C[Sn](C)(C)C>O1CCOCC1.CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:35][C:5]1[CH:4]=[CH:3][C:2]([CH3:38])=[CH:7][C:6]=1[C:8]1([S:22]([C:25]2[CH:26]=[N:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=2)(=[O:24])=[O:23])[CH2:13][CH2:12][CH:11]([NH:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])[CH2:10][CH2:9]1

Participants

8

Reactant 4

HCID 11661TetramethyltinHCID 25953Cesium fluorideHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 20781270HCID 20781270, compound

Product 1

HCID 20781242HCID 20781242, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

The compound prepared in Example 75 (50 mg) in dioxane was treated with cesium fluoride (2.2 equivalents), tri-tert-butylphosphine (12 mol %), tetramethyltin (2 equivalents), and Pd2(dba)3 (3 mol %) and heated at 100° C. for 3 h. The reaction mixture was cooled, diluted with ether, filtered and the filtrate evaporated in vacuo. Purification by column chromatography gave the toluene derivative (13 mg, 29%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate evaporated in vacuo
  4. customPurification by column chromatography
  5. customgave the toluene derivative (13 mg, 29%)

Sources & evidence

ORD record
ord-e5808a180fac4f5085308848a2a79509
Source dataset
uspto-grants-2005_05
Patent number
US06890956B2

Reaction notes

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