Hydrochloric Acid → HCID 67168298, compound

HRID 1517584Notes

Reaction equation

[CH2:1]([Zn]CC)C.CCCCCC.FC(F)(F)C(O)=O.ICI.[CH2:22]([O:24][C:25]([C:27]1[C:28]([CH3:42])=[N:29][N:30]([C:32]2[C:37]([CH2:38][O:39][CH:40]=[CH2:41])=[CH:36][CH:35]=[CH:34][N:33]=2)[CH:31]=1)=[O:26])[CH3:23].Cl>ClCCl>[CH:40]1([O:39][CH2:38][C:37]2[C:32]([N:30]3[CH:31]=[C:27]([C:25]([O:24][CH2:22][CH3:23])=[O:26])[C:28]([CH3:42])=[N:29]3)=[N:33][CH:34]=[CH:35][CH:36]=2)[CH2:1][CH2:41]1

Participants

Conditions

Temperature: 0 °C

Procedure

1.0 M diethylzinc in hexane (365.7 mL, 3.5 mmol) is added under nitrogen to dichloromethane (0.9 mL). The solution is cooled to 0° C. and a solution of trifluoroacetic acid (268.4 μL, 3.5 mmol) in dichloromethane (0.9 mL) is added very slowly. After 20 min a solution of diiodomethane (286.1 mL, 3.5 mmol) in dichloromethane (0.9 mL) is added. After an additional 20 min, a solution of 3-methyl-1-(3-vinyloxymethyl-pyridin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (510 mg, 1.8 mmol) in dichloromethane (0.9 mL) is added. The mixture is stirred at room temperature overnight. 5% HCl is added and the aqueous layer is extracted with ethyl acetate. The organic layer is separated, dried over sodium sulfate and the solvent is eliminated under reduced pressure. The crude is purified by normal phase Isco chromatography using hexane and ethyl acetate as eluents (5-20% in ethyl acetate) to get 310 mg of ethyl 1-[3-(cyclopropoxymethyl)-2-pyridyl]-3-methyl-pyrazole-4-carboxylate. MS (m/z): 302 (M+1)

Workup

extractionthe aqueous layer is extracted with ethyl acetate
customThe organic layer is separated
dry with materialdried over sodium sulfate
customThe crude is purified by normal phase Isco chromatography

Sources & evidence

ORD record: ord-4ca972fd360049f8a6dcd1cfba27d51f
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232289B2

Reaction notes

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