Acetonitrile → 1-(4'-methyl-[1,1'-biphenyl]-4-yl)-1H-pyrazole

HRID 923628Notes

Reaction equation

B(O)(O)[C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[CH:6][CH:7]=1.Br[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:22]=[CH:21][CH:20]=[N:19]2)=[CH:14][CH:13]=1.CC#N.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH:22]=[CH:21][CH:20]=[N:19]3)=[CH:14][CH:13]=2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 130 °C

Procedure

Prepared using General Procedure 16. A stirring mixture of p-tolylboronic acid (391 mg, 2.88 mmol) and 1-(4-bromophenyl)-1H-pyrazole (535 mg, 2.40 mmol) INT-84 in THF (4 mL), MeCN (4 mL) and sodium carbonate (1 M aqueous) (4.8 mL, 4.80 mmol) was de-gassed by bubbling through N2 gas. PdCl2dppf (88 mg, 0.120 mmol) was added and the reaction mixture further de-gassed. The reaction was heated at 130° C. for 30 min in a microwave. The mixture was cooled to room temperature, poured onto water (100 mL) and extracted with EA/THF (2×50/10 mL). The combined organic extracts were washed with brine (50 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography (EA/hexanes) to afford 315 mg (56%) of 1-(4′-methyl-[1,1′-biphenyl]-4-yl)-1H-pyrazole INT-85. LCMS-ESI (m/z) calculated for C16H14N2: 234; found 235 [M+H]+, tR=2.60 min (Method 10).

Workup

customPrepared
customby bubbling through N2 gas
temperatureThe mixture was cooled to room temperature
additionpoured onto water (100 mL)
extractionextracted with EA/THF (2×50/10 mL)
washThe combined organic extracts were washed with brine (50 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by chromatography (EA/hexanes)

Sources & evidence

ORD record: ord-4868ec0b59a744759ee8a11238305cd2
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278910B2

Reaction notes

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