Ethanol → HCID 59516062, compound

HRID 1799397Notes

Reaction equation

HRID 1799397 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][CH2:14][CH3:15])=[C:11]([C:16]([N:18]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH3:19])=[O:17])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.O1C[CH2:39][O:38][CH2:37][CH2:36]1.C([OH:43])C>CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd].CN(C1C=CN=CC=1)C.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[CH:20]1([N:18]([CH3:19])[C:16]([C:11]2[CH:10]=[N:9][N:8]([C:5]3[CH:6]=[CH:7][C:2]([C:39]([O:38][CH2:37][CH3:36])=[O:43])=[CH:3][CH:4]=3)[C:12]=2[CH2:13][CH2:14][CH3:15])=[O:17])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

8

Reactant 4

HCID 702EthanolHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 11739881HCID 11739881, compound2×

Product 1

HCID 59516062HCID 59516062, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)Catalyst

Conditions

Temperature
150 °C

Procedure

1-(4-chlorophenyl)-N-cyclohexyl-N-methyl-5-propyl-pyrazole-4-carboxamide (Intermediate #24), 101 mg, 0.28 mmol), Molybdenum hexacarbonyl (37 mg, 0.14 mmol), Herrmann's catalyst (Trans-Di-Mu-Acetatobis[2-(Di-O-Tolylphosphino)Benzyl]dipalladium(II), 14 mg, 0.01 mmol), DMAP (69 mg, 0.56 mmol), DIPEA (98 μL, 0.56 mmol), Fu's salt (Tri-(T-Butyl)Phosphonium Hydrogen tetrafluoroborate Salt, 17 mg, 0.06 mmol), Dioxane (2 mL), Ethanol (2 mL) were mixed into to a microwave tube. The reaction mixture was then heated at 150° C. for 1 hour by microwave.

Sources & evidence

ORD record
ord-8f67f0da62f3490ca9f988b55846095a
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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