tert-Butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylate → Tert-butyl 4-(6-{2-[4-(ethoxycarbonyl)-2-fluorophenyl]vinyl}pyridin-3-yl)piperazine-1-carboxylate

HRID 1465486Notes

Reaction equation

HRID 1465486 reaction equation
[Br-].[CH2:2]([O:4][C:5]([C:7]1[CH:32]=[CH:31][C:10]([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:9]([F:33])[CH:8]=1)=[O:6])[CH3:3].[CH:34]([C:36]1[N:41]=[CH:40][C:39]([N:42]2[CH2:47][CH2:46][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:44][CH2:43]2)=[CH:38][CH:37]=1)=O>>[CH2:2]([O:4][C:5]([C:7]1[CH:32]=[CH:31][C:10]([CH:11]=[CH:34][C:36]2[N:41]=[CH:40][C:39]([N:42]3[CH2:47][CH2:46][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:44][CH2:43]3)=[CH:38][CH:37]=2)=[C:9]([F:33])[CH:8]=1)=[O:6])[CH3:3]

Participants

3

Reactant 2

HCID 58181229tert-Butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylateHCID 86651846[4-(Ethoxycarbonyl)-2-fluorobenzyl](triphenyl)phosphonium bromide

Product 1

HCID 67030631Tert-butyl 4-(6-{2-[4-(ethoxycarbonyl)-2-fluorophenyl]vinyl}pyridin-3-yl)piperazine-1-carboxylateYield 98.9%

Procedure

By a method similar to Production Example 108, step 4, [4-(ethoxycarbonyl)-2-fluorobenzyl](triphenyl)phosphonium bromide (2.513 g, 4.802 mmol) and tert-butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylate (1.166 g, 4.002 mmol) were condensed to give tert-butyl 4-(6-{2-[4-(ethoxycarbonyl)-2-fluorophenyl]vinyl}pyridin-3-yl)piperazine-1-carboxylate (1.802 g, yield 98.9%, E/Z mixture) as a pale-brown solid.

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-1d6eec26c38443e490b3f0c632484e19
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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