2,2'-Bipyridine → 1,5-Dicyclopropyl-3-(2,5-dimethyl-pyrrol-1-yl)-1H-pyrazole

HRID 884614Notes

Reaction equation

N1C=CC=CC=1[C:7]1[CH:12]=[CH:11]C=CN=1.[CH:13]1([C:16]2[NH:20][N:19]=[C:18]([N:21]3[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[CH3:27])[CH:17]=2)[CH2:15][CH2:14]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:11]1([N:20]2[C:16]([CH:13]3[CH2:15][CH2:14]3)=[CH:17][C:18]([N:21]3[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[CH3:27])=[N:19]2)[CH2:12][CH2:7]1

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of copper (II) acetate (0.902 g, 4.97 mmol) and 2,2′-bipyridine (0.776 g, 4.97 mmol) in DCE (20 mL) is stirred at 70° C. for 15 min, then transferred to a suspension of cyclopropyl trifluoroborate potassium salt (1.47 g, 9.94 mmol) and 5-Cyclopropyl-3-(2,5-dimethyl-pyrrol-1-yl)-1H-pyrazole (1 g, 4.97 mmol), and sodium carbonate (1.053 g, 9.94 mmol) in DCE (40 mL). The resulting dark-green mixture is stirred at 70° C. for 24 h. T The reaction mixture is partitioned between EtOAc and 1N HCl. The aqueous layer is extracted with EtOAc. The combined organic layers are washed with brine, dried (Na2SO4) and concentrated. The residue (1.64 g) is purified by ISCO (EtOAc-heptane 0-30%) to provide the desired product (1.25 g) as a colorless oil. MS (ESI) m/z 242.3 (M+1).

Workup

stirringThe resulting dark-green mixture is stirred at 70° C. for 24 h
customT The reaction mixture is partitioned between EtOAc and 1N HCl
extractionThe aqueous layer is extracted with EtOAc
washThe combined organic layers are washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue (1.64 g) is purified by ISCO (EtOAc-heptane 0-30%)

Sources & evidence

ORD record: ord-3161064b3f39418b98ca739ce821f911
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242125B2

Reaction notes

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