Pyrazole → 2-[(1S)-6-(1H-Pyrazol-1-yl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethanol

HRID 2056781Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[C@H:10]([CH2:11][CH2:12][OH:13])[O:9][CH2:8][CH2:7][C:6]=2[CH:14]=1.[NH:15]1[CH:19]=[CH:18][CH:17]=[N:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I>[N:15]1([C:2]2[CH:3]=[CH:4][C:5]3[C@H:10]([CH2:11][CH2:12][OH:13])[O:9][CH2:8][CH2:7][C:6]=3[CH:14]=2)[CH:19]=[CH:18][CH:17]=[N:16]1

Participants

Conditions

Temperature: 150 °C

Procedure

2-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol (0.54 g, 2.1 mmol), pyrazole (0.29 g, 4.3 mmol), copper(I) iodide (0.062 g, 0.33 mmol) and potassium carbonate (0.30 g, 2.2 mmol) were stirred in dry DMF (3 mL) under nitrogen and heated at 150° C. for 18 h. The reaction mixture was cooled and extracted from water into dichloromethane. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The crude product was used in the next step without further purification.

Workup

temperatureThe reaction mixture was cooled
extractionextracted from water into dichloromethane
dry with materialThe combined organic extracts were dried (MgSO4)
filtrationfiltered
customevaporated in vacuo
customThe crude product was used in the next step without further purification

Sources & evidence

ORD record: ord-8d3eba1569f34598ba8586f5a24c1918
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07335660B2

Reaction notes

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