Tetrahydrofuran → HCID 71224836, compound

HRID 1918198Notes

Reaction equation

HRID 1918198 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:24]=[C:11]3[CH:12]=[C:13]([C:16]4[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=4)C=O)[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.C1([Mg]Br)CC1.[O:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:24]=[C:11]3[CH:12]=[C:13]([C:16]4[CH:17]=[C:18]([C:33]5([CH2:34][OH:30])[CH2:31][CH2:32]5)[CH:21]=[CH:22][CH:23]=4)[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 86675961HCID 86675961, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 71224836HCID 71224836, compoundYield 59%

Procedure

The procedure described in stage 6.2 is followed. Starting from 0.15 g (0.45 mmol) of 3-[2-(4-chlorophenyl)pyrazolo[1,5-a]pyridin-5-yl]benzaldehyde, obtained according to the process described in 6.1, in solution in 8 ml of tetrahydrofuran, followed by addition of 1.80 ml (0.9 mmol) of a cyclopropylmagnesium bromide solution (0.5M in tetrahydrofuran) and after chromatographing on silica gel, elution being carried out with a mixture of cyclohexane and ethyl acetate (8/2), 0.1 g (59%) of the expected product is obtained in the form of a beige powder.

Workup

  1. customobtained
  2. washafter chromatographing on silica gel, elution
  3. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (8/2)

Sources & evidence

ORD record
ord-5fe0e32df4914d1eb86b7f41383e67a9
Source dataset
uspto-grants-2013_12
Patent number
US08618301B2

Reaction notes

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