2-Methoxyphenethyl alcohol → 3-(5-(2-methoxyphenethoxy)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzonitrile

HRID 2196558Notes

Reaction equation

HRID 2196558 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])[N:5]=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:3]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH3:33][O:34][C:35]1[CH:43]=[CH:42][CH:41]=[CH:40][C:36]=1[CH2:37][CH2:38]O>C1COCC1>[CH3:33][O:34][C:35]1[CH:43]=[CH:42][CH:41]=[CH:40][C:36]=1[CH2:37][CH2:38][O:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])[N:5]=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:3]=1

Participants

5

Reactant 3

HCID 819092-Methoxyphenethyl alcoholHCID 5363146Diisopropyl azodicarboxylateHCID 178509828HCID 178509828, compound

Product 1

HCID 693009123-(5-(2-methoxyphenethoxy)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzonitrileYield 28.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 130 (200 mg, 0.790 mmol) and PS-PPh2 (2.15 mmol/g, 0.522 g, 1.5 eq, polymer supported triphenylphosphine) in THF (7 mL) under a nitrogen atmosphere was stirred for 10 minutes. DIAD (0.154 mL, 0.790 mmol) was added and after 1 hour of stirring at room temperature 2-methoxy-phenethyl alcohol (0.112 mL, 0.790 mmol) was added and the suspension was stirred for 48 h. The reaction mixture was filtered and the resin washed with DCM, the filtrate was concentrated and the residue purified by silica gel chromatography (Biotage 25M, 5-20% ethyl acetate in hexanes) to give 131 (86 mg, 0.222 mmol, 28.1% yield) as white solid. LRMS(ESI): (calc.) 387.4 (found) 388.1 (MH)+, 410.0 (MNa)+.

Workup

  1. additionwas added
  2. stirringthe suspension was stirred for 48 h
  3. filtrationThe reaction mixture was filtered
  4. washthe resin washed with DCM
  5. concentrationthe filtrate was concentrated
  6. customthe residue purified by silica gel chromatography (Biotage 25M, 5-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-83dd8b3322f14265b68c7d3fc8bca2bf
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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