5-(4-Chlorophenyl)-4-(pyridin-4-yl)-1-(2-trimethylsilylethoxy)methylpyrazole → HCID 178418738, compound

HRID 9884Notes

Reaction equation

HRID 9884 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](COCC[Si](C)(C)C)[N:11]=[CH:10][C:9]=2[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.BrC1C(C2C=CN=CC=2)=C(C2C=CC(F)=CC=2)NN=1.[CH2:46]1[C@@H:54]2[N:49]([CH2:50][CH2:51][C:52](=O)[CH2:53]2)[CH2:48][CH2:47]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][N:11]=[C:10]([C:52]3[CH2:53][C@H:54]4[N:49]([CH2:48][CH2:47][CH2:46]4)[CH2:50][CH:51]=3)[C:9]=2[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 219884875-(4-Chlorophenyl)-4-(pyridin-4-yl)-1-(2-trimethylsilylethoxy)methylpyrazoleHCID 45087810(S)-1,2,3,5,6,7,8,8a-octahydroindolizin-7-oneHCID 178418951HCID 178418951, compound

Product 1

HCID 178418738HCID 178418738, compoundYield 4%

Procedure

Following a procedure similar to that described in Example 2-2), but using 5-(4-chlorophenyl)-4-(pyridin-4-yl)-1-(2-trimethylsilylethoxy)methylpyrazole prepared as described in 1) instead of 3-bromo-5-(4-fluorophenyl)-4-(pyridin-4-yl)pyrazole, and using (S)-1,2,3,5,6,7,8,8a-octahydroindolizin-7-one instead of (±)-1,2,3,5,6,7,8,8a-octahydroindolizin-7-one, the resulting product was subjected to a dehydration reaction as described in Example 3 and then treated by column chromatography through silica gel (eluent, ethyl acetate:methanol:isopropylamine=10:1:1), to give the title compound (Rf=0.50, 357 mg) as a pale brown powder (yield 4%).

Workup

  1. customprepared
  2. customthe resulting product was subjected to a dehydration reaction
  3. additiontreated by column chromatography through silica gel (eluent, ethyl acetate:methanol:isopropylamine=10:1:1)

Sources & evidence

ORD record
ord-a6937d3243994fd38024ea9b8260c2c5
Source dataset
uspto-grants-2006_08
Patent number
US07091352B2

Reaction notes

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