Water → 4-[6-(2-Benzyloxycarbonylaminoethyloxy)-3-cyanoindol-1-yl]-2-methoxymethoxy-benzoic acid ethyl ester

HRID 1674600Notes

Reaction equation

HRID 1674600 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([OH:20])[CH:18]=3)[C:13]([C:21]#[N:22])=[CH:12]2)=[CH:7][C:6]=1[O:23][CH2:24][O:25][CH3:26])[CH3:2].[CH2:28]([O:35][C:36](=[O:41])[NH:37][CH2:38][CH2:39]Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:39][CH2:38][NH:37][C:36]([O:35][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:41])[CH:18]=3)[C:13]([C:21]#[N:22])=[CH:12]2)=[CH:7][C:6]=1[O:23][CH2:24][O:25][CH3:26])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 278694benzyl N-(2-bromoethyl)carbamateHCID 584375264-(3-Cyano-6-hydroxyindol-1-yl)-2-methoxymethoxybenzoic acid ethyl ester

Product 1

HCID 584372394-[6-(2-Benzyloxycarbonylaminoethyloxy)-3-cyanoindol-1-yl]-2-methoxymethoxy-benzoic acid ethyl esterYield 72.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(3-cyano-6-hydroxyindol-1-yl)-2-methoxymethoxybenzoic acid ethyl ester (0.37 g) in N,N-dimethylformamide (10 mL) were added (2-bromoethyl)carbamic acid benzyl ester (0.39 g) and potassium carbonate (0.28 g), and this mixture was stirred at 50° C. overnight. This reaction mixture was poured into water, and the precipitated solid was collected by filtration. This solid was washed with methanol, and dried to give the title compound (0.40 g).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washThis solid was washed with methanol
  3. customdried

Sources & evidence

ORD record
ord-ba5d0b76704e4b9e936ee792a195c832
Source dataset
uspto-grants-2011_08
Patent number
US08003647B2

Reaction notes

Loading…