Tetramethyltin → HCID 22462656, compound

HRID 1387055Notes

Reaction equation

HRID 1387055 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[C:5]([O:7][CH3:8])=[O:6].[CH3:18][Sn](C)(C)C>C1(C)C=CC=CC=1.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>[CH3:18][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 11661TetramethyltinHCID 10803994Methyl 3-bromo-4-(pyrrolidin-1-ylmethyl)benzoate

Product 1

HCID 22462656HCID 22462656, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
137.5 °C

Procedure

A solution of methyl 3-bromo-4-[(1-pyrrolidinyl)methyl]benzoate (16 g, 53.7 mmol) in 110 mL of toluene was treated with Pd(PPh3)4 (3.1 g, 2.68 mmol) and tetramethyltin (22.3 mL, 161.1 mmol). The resulting mixture was heated at 135-140° C. for 36 hr in a sealed tube. After cooling to ambient temperature, the reaction mixture was filtered through diatomaceous earth and concentrated in vacuo. The crude brown residue was purified by PrepLC (SiO2; 97:2:1 hexanes-THF-TEA) to afford 11.4 g (48.9 mmol; 91%) of the title compound as a slightly yellow oil.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe reaction mixture was filtered through diatomaceous earth
  3. concentrationconcentrated in vacuo
  4. customThe crude brown residue was purified by PrepLC (SiO2; 97:2:1 hexanes-THF-TEA)

Sources & evidence

ORD record
ord-f2e11b0d4dcb483c97ba733262bdb691
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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