HCID 87357812, compound → HCID 87358663, compound

HRID 926927Notes

Reaction equation

HRID 926927 reaction equation
C([N:4]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Sn:15]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])=[C:11]([C:28]([O:37][CH2:38][O:39][CH3:40])([C:33]([F:36])([F:35])[F:34])[C:29]([F:32])([F:31])[F:30])[CH:10]=1)CC=C)C=C>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:32][C:29]([F:30])([F:31])[C:28]([C:11]1[CH:10]=[C:9]([CH2:8][NH2:4])[CH:14]=[CH:13][C:12]=1[Sn:15]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])([O:37][CH2:38][O:39][CH3:40])[C:33]([F:36])([F:35])[F:34]

Participants

4

Reactant 1

HCID 87357812HCID 87357812, compound

Product 1

HCID 87358663HCID 87358663, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

Compound 7 (622 mg, 906 μmol) was dissolved in dichloromethane (10 mL) and the solution was degassed by nitrogen bubbling over 15 min. The solution was then added to N,N-dimethylbarbituric acid (849 mg, 5.44 mmol) and Tetrakis(triphenylphosphine)palladium(0) (21 mg 18.1 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 (20 mL), and washed with a 0.1M sodium carbonate solution (3×10 mL). The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified over silica gel using dichloromethane/methanol (95/5) to give 423 mg (698 μmol, 77% 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 (20 mL)
  4. washwashed with a 0.1M sodium carbonate solution (3×10 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-8e14154a277f4691a6901b35b2d7516d
Source dataset
uspto-grants-2016_03
Patent number
US09290421B2

Reaction notes

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