Styrene → HCID 67462533, compound

HRID 1619956Notes

Reaction equation

HRID 1619956 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[CH:21]=[C:20]([C:22]4[CH:27]([CH2:28][CH3:29])[CH2:26][C:25](=[O:30])[NH:24][N:23]=4)[CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][CH:8]=1)(=O)=O.[CH2:33]=[CH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[CH2:28]([CH:27]1[C:22]([C:20]2[CH:19]=[CH:18][C:16]3[N:17]=[C:13]([C:10]4[CH:9]=[CH:8][C:7]([CH:33]=[CH:34][C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)=[CH:12][CH:11]=4)[O:14][C:15]=3[CH:21]=2)=[N:23][NH:24][C:25](=[O:30])[CH2:26]1)[CH3:29]

Participants

8

Reactant 4

HCID 7501Styrene2×HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphine2×HCID 86689064HCID 86689064, compound

Product 1

HCID 67462533HCID 67462533, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst2×HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

60 mg (128 μmol) 4-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-benzoxazol-2-yl]-phenyl trifluoro-methanesulphonate, 14.7 μl (128 μmol) styrene, 2.9 mg (13 μmol) palladium-(II)-acetate, 4.1 mg (13 μmol) tri-o-tolylphosphine, 72 μl (513 μmol) triethylamine and 2 ml acetonitrile are combined and stirred overnight at 80° C. Then a further 7.5 μl styrene, 2.9 mg palladium-(II)-acetate and 4 mg tri-o-tolyphosphine are added and the mixture is stirred for 5 days at 80° C. Then it is diluted with DCM and extracted successively with 10% sodium carbonate solution and sat. saline solution. The org. phase is evaporated down completely i.V. and the residue is purified through silica gel (eluant: DCM/methanol). The residue obtained is crystallised from cyclohexane/EA.

Workup

  1. stirringthe mixture is stirred for 5 days at 80° C
  2. extractionextracted successively with 10% sodium carbonate solution and sat. saline solution
  3. customphase is evaporated down completely i.V
  4. customand the residue is purified through silica gel (eluant: DCM/methanol)
  5. customThe residue obtained
  6. customis crystallised from cyclohexane/EA

Sources & evidence

ORD record
ord-7d6c52f3760b494c8c6deee24b294e4c
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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