(6-(1H-Pyrazol-1-yl)pyridin-3-yl)methanol synthesis
- Product Name:(6-(1H-Pyrazol-1-yl)pyridin-3-yl)methanol
- CAS Number:748796-38-5
- Molecular formula:C9H9N3O
- Molecular Weight:175.19
288-13-1
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21543-49-7
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748796-38-5
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Yield:748796-38-5 95%
Reaction Conditions:
with potassium carbonate;copper(l) iodide;trans-N,N'-dimethyl-1,2-cyclohexanediamine at 110; for 44 h;
Steps:
6
Example 6 Preparation of (6-Pyrazol-1-yl-pyridin-3-yl)-methanol (III); Copper(I) iodide (65 mg, 0.34 mmol, 22 mol %), pyrazole (411 mg, 6.04 mmol, 3.8 eq), potassium carbonate (705 mg, 5.10 mmol, 3.2 eq), (6-Chloro-pyridin-3-yl)-methanol (227 mg, 1.58 mmol) and rac-trans-N,N'-dimethylcyclohexane-1,2-diamine (92 mg, 0.65 mmol, 41 mol %) were mixed together and stirred at 110° C. for 44 hours. After cooling down, the mixture was dissolved in ethyl acetate and water (1:1, v/v, 10 ml). The organic phase was separated, dried over sodium sulfate and concentrated. Column chromatography (EtOAc:hexanes, 1:1) of the residue afforded the product as a light brown oil 292 mg (corrected yield: 95%), which was good for the next reaction although containing 10 wt % pyrazole by 1H NMR. MS-ESI m/z 175.97 (M+H)+; 1H NMR (CDCl3) δ 8.58 (s, 1H), 8.39 (s, 1H), 7.95 (d, 1H), 7.84 (d, 1H), 7.73 (s, 1H), 6.46 (s, 1H), 3.74 (s, 2H) ppm.
References:
US2006/247440,2006,A1 Location in patent:Page/Page column 10; 13-14
321533-62-4
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748796-38-5
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23100-12-1
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748796-38-5
41 suppliers
$45.00/50mg