tert-Butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylate → tert-butyl 4-[6-(2-{5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]thiophen-3-yl}vinyl)pyridin-3-yl]piperazine-1-carboxylate

HRID 1465505Notes

Reaction equation

HRID 1465505 reaction equation
[Cl-].[CH3:2][O:3][C:4](=[O:32])/[CH:5]=[CH:6]/[C:7]1[S:11][CH:10]=[C:9]([CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:8]=1.[CH:33]([C:35]1[N:40]=[CH:39][C:38]([N:41]2[CH2:46][CH2:45][N:44]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:43][CH2:42]2)=[CH:37][CH:36]=1)=O>>[CH3:2][O:3][C:4](=[O:32])/[CH:5]=[CH:6]/[C:7]1[S:11][CH:10]=[C:9]([CH:12]=[CH:33][C:35]2[N:40]=[CH:39][C:38]([N:41]3[CH2:46][CH2:45][N:44]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:43][CH2:42]3)=[CH:37][CH:36]=2)[CH:8]=1

Participants

3

Reactant 2

HCID 58181229tert-Butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylateHCID 86651854({5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]thiophen-3-yl}methyl)(triphenyl)phosphonium chloride

Product 1

HCID 67267141tert-butyl 4-[6-(2-{5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]thiophen-3-yl}vinyl)pyridin-3-yl]piperazine-1-carboxylateYield 94.8%

Procedure

By a method similar to Production Example 108, step 4, ({5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]thiophen-3-yl}methyl)(triphenyl)phosphonium chloride (1.724 g, 3.600 mmol) and tert-butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylate (874.1 mg, 3.000 mmol) were condensed to give tert-butyl 4-[6-(2-{5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]thiophen-3-yl}vinyl)pyridin-3-yl]piperazine-1-carboxylate (1.295 g, yield 94.7%) as a yellow oil.

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-09bb4f93b02842898be353e8c8a761d7
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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