Water → HCID 86626078, compound

HRID 390598Notes

Reaction equation

HRID 390598 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].C(N(C(C)C)CC)(C)C.[CH2:23]([O:25]/[C:26](=[CH:32]\[C:33]1[CH:34]=[N:35][C:36]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([NH:45][CH3:46])[CH:40]=2)=[CH:37][CH:38]=1)/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:24].O>ClCCl>[CH2:23]([O:25]/[C:26](=[CH:32]\[C:33]1[CH:34]=[N:35][C:36]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([N:45]([CH3:46])[C:2]([O:4][C:5]3[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=3)=[O:3])[CH:40]=2)=[CH:37][CH:38]=1)/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 86626076HCID 86626076, compound

Product 1

HCID 86626078HCID 86626078, compoundYield 118.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.17 g (0.83 mmol) of 4-nitrophenyl chloroformate and then 0.14 mL (0.83 mmol) of diisopropylethylamine are added to a solution of 0.18 g (0.55 mmol) of ethyl (Z)-2-ethoxy-3-[6-(3-methylaminophenyl)pyrid-3-yl]acrylate in 5 mL of dichloromethane. The reaction mixture is stirred for 1 hour 30 minutes at room temperature. The reaction is stopped by addition of 5 mL of water and extraction with dichloromethane. The organic phases are combined and then dried over magnesium sulfate. The solvents are evaporated off. 0.32 g (100%) of ethyl (Z)-2-ethoxy-3-(6-{3-[methyl-(4-nitrophenoxycarbonyl)amino]phenyl}pyrid-3-yl)acrylate is obtained in the form of a yellow oil. The crude product obtained is used directly in the following step.

Workup

  1. dry with materialdried over magnesium sulfate
  2. customThe solvents are evaporated off

Sources & evidence

ORD record
ord-107b1daef1924bd9a64d8d8289ff43b1
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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