Z-4-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester → Z-3-[2-(1-tert-Butoxycarbonyl-piperidin-4-yloxy)-5-chloro-benzylidene]-6-chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

HRID 504466Notes

Reaction equation

HRID 504466 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2/[CH:22]=[C:23]2\[C:24](=[O:33])[NH:25][C:26]3[C:31]\2=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6]([N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)/[C:23](=[CH:22]/[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[O:14][CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)/[C:24]1=[O:33])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86632056Z-4-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86632057Z-3-[2-(1-tert-Butoxycarbonyl-piperidin-4-yloxy)-5-chloro-benzylidene]-6-chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl esterYield 183.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of E/Z-4-[4-Chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (2.44 g, 5 mmol) in DCM (10 mL) at r.t. was added diteret-butyl-dicarbonate (1.6 g, 7.5 mmol), followed by the addition of 4-dimethylaminopyridine (0.06 g, 0.5 mmol). The reaction mixture was stirred for 2 h and washed with 0.5N hydrochloric acid, dried over anhydrous Na2SO4, then the solvent was removed to give title compound (Yield: 2.7 g, 92%).

Workup

  1. washwashed with 0.5N hydrochloric acid
  2. dry with materialdried over anhydrous Na2SO4
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-711cf83a594a4401aefd00d0535a7b61
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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