N-(3-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-4-(tributyl-stannyl)benzyl)-N-methylprop-2-en-1-amine → (3-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-4-(tri butyl-stannyl)phenyl)-N-methylmethanamine

HRID 926931Notes

Reaction equation

HRID 926931 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]([C:12]1[CH:13]=[C:14]([CH:21]=[CH:22][C:23]=1[Sn:24]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:15][N:16](C)[CH2:17]C=C)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]>ClCCl.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>[F:38][C:2]([F:1])([F:37])[C:3]([C:12]1[CH:13]=[C:14]([CH2:15][NH:16][CH3:17])[CH:21]=[CH:22][C:23]=1[Sn:24]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]

Participants

4

Reactant 1

HCID 87358460N-(3-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-4-(tributyl-stannyl)benzyl)-N-methylprop-2-en-1-amine

Product 1

HCID 87358059(3-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-4-(tri butyl-stannyl)phenyl)-N-methylmethanamineYield 78.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

Compound 13 (270 mg, 409 μmol) was dissolved in dichloromethane (5 mL) and the solution was degassed by nitrogen bubbling over 15 min. The solution was then added to N,N-dimethylbarbituric acid (191 mg, 1.23 mmol) and Tetrakis(triphenylphosphine)palladium(0) (19 mg 16.4 μmol) placed in a two necked flask under nitrogen atmosphere and the resulting mixture was warmed 4 h at 35° C. The solvent was removed under vacuum, the residue dissolved in diethylether (10 mL), and washed with a 0.1M sodium carbonate solution (2×5 mL). The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified over silica gel using chloroform/methanol (9/1) to give 199 mg (321 μmol, 78% yield) of a yellowish oil.

Workup

  1. customthe solution was degassed by nitrogen bubbling over 15 min
  2. customThe solvent was removed under vacuum
  3. dissolutionthe residue dissolved in diethylether (10 mL)
  4. washwashed with a 0.1M sodium carbonate solution (2×5 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified over silica gel

Sources & evidence

ORD record
ord-5d9bb736d8484e9aa14ae9218a2bbee4
Source dataset
uspto-grants-2016_03
Patent number
US09290421B2

Reaction notes

Loading…