1-(4-Aminophenyl)-3-(3-pyridyl)-5-ethylpyrazole → 6-[(3-Cyanopropoxy)napthalen-1-yl]-[4-(5-ethyl-3-pyridin-3-yl-pyrazol-1-yl)phenyl]amine

HRID 1634106Notes

Reaction equation

HRID 1634106 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2I)[CH:8]=1)#[N:2].[CH2:18]([C:20]1[N:24]([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[N:23]=[C:22]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[CH:21]=1)[CH3:19].O(C(C)(C)C)[Na]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:29]1[C:28]([NH2:31])=[CH:27][CH:26]=[C:25]([N:24]2[C:20]([CH2:18][CH3:19])=[CH:21][C:22]([C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)=[N:23]2)[CH:30]=1)#[N:2]

Participants

7

Reactant 3

HCID 186770941-(4-Aminophenyl)-3-(3-pyridyl)-5-ethylpyrazoleHCID 186771322-(3-Cyanopropoxy)-5-iodonaphthaleneHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 186771136-[(3-Cyanopropoxy)napthalen-1-yl]-[4-(5-ethyl-3-pyridin-3-yl-pyrazol-1-yl)phenyl]amineYield 90.8%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(3-cyanopropoxy)-5-iodonaphthalene (77.0 mg, 0.228 mmol), with 5-ethyl-3-(3-pyridyl)-1-(4′-aminophenyl)pyrazole (72.4 mg, 1.2 equiv.), NaO-t-Bu (40.8 mg, 1.86 equiv.), Pd2(dba)3 (5.2 mg, 2.5% equiv.) and (−)B1NAP (10.6 mg, 7.5% equiv.) in toluene (1 mL) was heated at 80° C. for 18 h. The mixture was diluted with ethyl acetate, filtered through diatomaceous earth and concentrated. Chromatography on silica gel gave the title compound (98.0 mg, 90.8%). 1H-NMR (CDCl3): 1.30 (t, J=7.4 Hz, 3H), 2.20-2.25 (m, 2H), 2.62-2.74 (m, 4H), 4.22 (t, J=5.4 Hz, 2H), 6.31 (bs, 1H), 6.59 (s, 1H), 6.99 (d, J=8.6 Hz, 2H), 7.17 (d, J=9.1 Hz, 1H), 7.20 (s, 1H), 7.29-7.34 (m, 4H), 7.43 (t, J=8.0 Hz, 1H), 7.56 (d, J=8.2 Hz, 1H), 7.98 (d, J=9.2 Hz, 1H), 8.21 (d, J=7.9 Hz, 1H), 8.56 (d, J=4.2 Hz, 1H), 9.11 (s, 1H).

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0d4c975f1b6f4c378c3e5cd6d67ce0a7
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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