Tetramethyltin → 7-(1-Ethylpropyl)-1,4-dimethyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 1698563Notes

Reaction equation

HRID 1698563 reaction equation
Br[C:2]1[C:10]2[NH:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=2[C:5]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:4][CH:3]=1.[CH3:18][Sn](C)(C)C>CN(C)P(=O)(N(C)C)N(C)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:14]([CH:13]([C:5]1[C:6]2[N:7]([CH3:12])[C:8](=[O:11])[NH:9][C:10]=2[C:2]([CH3:18])=[CH:3][CH:4]=1)[CH2:16][CH3:17])[CH3:15]

Participants

6

Reactant 2

HCID 11661TetramethyltinHCID 672727554-bromo-7-(1-ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 672728947-(1-Ethylpropyl)-1,4-dimethyl-1,3-dihydro-2H-benzimidazol-2-oneYield 57.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 4-bromo-7-(1-ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (250 mg, 0.84 mmol), tetrakis(triphenylphosphine)palladium (194 mg, 0.168 mmol), tetramethyltin (1.16 mL, 8.4 mmol) in hexamethylphosphoric triamide (5 mL) was refluxed for 18 h. After cooling, the mixture was diluted with water and extracted with dichloromethane. The organics were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on a silica gel (n-hexane/ethyl acetate=90:10-50:50) to give the title compound (111 mg, 0.48 mmol, 57%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on a silica gel (n-hexane/ethyl acetate=90:10-50:50)

Sources & evidence

ORD record
ord-f2d66bba8b4b49af8722f6f883f468b5
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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