Toluene → HCID 54116455, compound

HRID 279071Notes

Reaction equation

HRID 279071 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[C:17]3[CH2:21][CH2:20][N:19]([C:22]4[CH:23]=N[CH:25]=[CH:26][CH:27]=4)[C:18]3=[O:28])[CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:9]2)=[CH:4][CH:3]=1.[C:29]1(C)C=CC=CC=1>C(N(CC)CC)C.Cl[Pd]Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[C:17]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:29][CH:23]=4)[C:18]3=[O:28])[CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 1140Toluene2×HCID 86585109HCID 86585109, compound

Product 1

HCID 54116455HCID 54116455, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of intermediate 4b (370 g) in toluene (5.2 lit), Triethylamine (248 ml), Triphenilphosphine (7.4 g) and PdCl2 (2.52 g) were added. The resulting solution was warmed to 100° C. and stirred for 2 h. The suspension was chilled to 20-25 ° C. and toluene (2.6 ml) was added. The reaction mixture was washed with NH4Cl 8% (3×5.2 lit) and water (5.2 lit). The organic layer was filtered over a celite pad and it was washed with toluene (1 lit); then it was distilled under vacuum (T=50° C.; P=60 mbar) to reach 6.3 lit. After cooling to T=20-25° C., isooctane (5.2 lit) was dropped over 30 min. The precipitate was stirred for 2 h 30 min then it was filtered and washed with a mixture toluene/isooctane 1/1 (1.85 lit). The yellow solid was dried in vacuum at T=40° C. for 18 h to obtain the title compound as a yellow solid 210 g.

Workup

  1. temperatureThe suspension was chilled to 20-25 ° C.
  2. washThe reaction mixture was washed with NH4Cl 8% (3×5.2 lit) and water (5.2 lit)
  3. filtrationThe organic layer was filtered over a celite pad and it
  4. washwas washed with toluene (1 lit)
  5. distillationthen it was distilled under vacuum (T=50° C.; P=60 mbar)
  6. temperatureAfter cooling to T=20-25° C., isooctane (5.2 lit)
  7. additionwas dropped over 30 min
  8. stirringThe precipitate was stirred for 2 h 30 min
  9. filtrationit was filtered
  10. washwashed with a mixture toluene/isooctane 1/1 (1.85 lit)
  11. customThe yellow solid was dried in vacuum at T=40° C. for 18 h

Sources & evidence

ORD record
ord-ae1179fa3edc46f095fbffa8283d9521
Source dataset
uspto-grants-2002_03
Patent number
US06362199B1

Reaction notes

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