Cesium carbonate → (1-(3-bromo-4-methoxyphenyl)-1H-pyrazol-3-yl)methanol

HRID 1027274

Reaction equation

N1C=CC=CC=1C1NC2C=CC=CC=2N=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:22]1[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[N:23]1.[Br:29][C:30]1[CH:35]=[C:34](I)[CH:33]=[CH:32][C:31]=1[O:37][CH3:38]>CCOC(C)=O.[Cu]I.CN(C=O)C>[Br:29][C:30]1[CH:35]=[C:34]([N:22]2[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[N:23]2)[CH:33]=[CH:32][C:31]=1[O:37][CH3:38]

Participants

Conditions

Temperature: 60 °C

Procedure

To a 100 mL round bottom flask was added copper (I) iodide (30.4 mg, 0.16 mmol), 2-(2-pyridyl)benzimidazole (31.2 mg, 0.16 mmol), cesium carbonate (625 mg, 1.92 mmol) and DMF (5.3 mL). The reaction mixture was heated to 60° C. for 1 h then (1H-pyrazol-3-yl)methanol (235 mg, 2.40 mmol) and 2-bromo-4-iodo-1-methoxybenzene (500 mg, 1.60 mmol) were added and the mixture was heated at 100° C. for 18 hours. The reaction was cooled, diluted with EtOAc and filtered through celite. The filtrate was concentrated in vacuo and purified by silica gel chromatography (0-100% EtOAc in Hepane) to afford (1-(3-bromo-4-methoxyphenyl)-1H-pyrazol-3-yl)methanol (353 mg) MS [M+2H+]=285.0.

Workup

temperaturethe mixture was heated at 100° C. for 18 hours
temperatureThe reaction was cooled
filtrationfiltered through celite
concentrationThe filtrate was concentrated in vacuo
custompurified by silica gel chromatography (0-100% EtOAc in Hepane)

Sources & evidence

ORD record: ord-defd10b236444fda9f9906956cc2d1e5
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729263B2

Linked notes

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