Sodium Carbonate → 4-(4-fluorophenyl)-3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine

HRID 915568Notes

Reaction equation

Br[C:2]1[C:3]([CH3:15])=[N:4][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[C:6]=1[NH2:7].[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.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:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[C:3]([CH3:15])=[N:4][N:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH3:14])[C:6]=2[NH2:7])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 110 °C

Procedure

4-Bromo-3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine (2 g, 7.52 mmol), 4-fluorophenylboronic acid (2.10 g, 11.3 mmol), and Pd(PPh3)4 (434 mg, 0.38 mmol) were dissolved in DMF (20 mL), and Na2CO3 (saturated aq solution, 18 mL) was added. The mixture was degassed for 10 min and then heated at 110° C. for 2 h. The reaction mixture was diluted, and the solid was filtered off. The solvent was concentrated under reduced pressure, and the residue purified by silica gel flash chromatography using 10 to 40% ethyl acetate in hexanes to give 1.2 g (90% pure, 51%) of the title compound. 1H NMR (300 MHz, CD2Cl2) δ 7.25-7.34 (m, 6H), 7.08 (t, 2H), 3.62 (s, 2H), 2.20 (s, 3H), 2.14 (s, 3H).

Workup

customThe mixture was degassed for 10 min
additionThe reaction mixture was diluted
filtrationthe solid was filtered off
concentrationThe solvent was concentrated under reduced pressure
customthe residue purified by silica gel flash chromatography

Sources & evidence

ORD record: ord-49082bd0229249a6b466f329552c99c9
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265144B2

Reaction notes

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