Sodium Iodide → HCID 89813074, compound

HRID 1480961Notes

Reaction equation

HRID 1480961 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[CH2:12]Br)[CH3:2].[CH2:15]([O:17][C:18](=[O:32])[CH2:19][NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=1[O:30][CH3:31])[CH3:16].[Na+].[I-].CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[CH2:12][N:20]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=1[O:30][CH3:31])[CH2:19][C:18]([O:17][CH2:15][CH3:16])=[O:32])[CH3:2]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 19895532Ethyl 2-(2,4-dimethoxybenzylamino)acetateHCID 22616360HCID 22616360, compound

Product 1

HCID 89813074HCID 89813074, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-bromo-2-bromomethyl-benzoic acid ethyl ester (34.3 g, prepared according to Zhong, Min and Li, Leping PCT Int. Appl., 2010065674, 10 Jun. 2010), (2,4-dimethoxy-benzylamino)-acetic acid ethyl ester (32.4 g), NaI (1.6 g), DIPEA (27.8 mL) in DMF was stirred at rt overnight. Then the reaction mixture was diluted with EtOAc, washed with water, diluted NaCl, dried over sodium sulfate, filtered, concentrated and column purified to give the desired product (36.14 g). LC MS ESI+: 495 (M+1)+.

Workup

  1. washwashed with water, diluted NaCl
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customcolumn purified

Sources & evidence

ORD record
ord-10299502a51c4c2d8fc390e105face50
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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