Triethylamine → methyl 2-(4-(5-((2,4-dichlorophenethyl)carbamoyl)-1H-indol-1-yl)-3-cyanophenyl)acetate

HRID 1810102Notes

Reaction equation

HRID 1810102 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:5][C:4]=1[N:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23](O)=[O:24])=[CH:20][CH:21]=2)[CH:16]=[CH:15]1)#[N:2].C(N(CC)CC)C.C(Cl)(=O)C(Cl)=O.[Cl:39][C:40]1[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:41]=1[CH2:47][CH2:48][NH2:49]>C(Cl)Cl.CN(C=O)C>[Cl:39][C:40]1[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:41]=1[CH2:47][CH2:48][NH:49][C:23]([C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[N:14]([C:4]1[CH:5]=[CH:6][C:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:3]=1[C:1]#[N:2])[CH:15]=[CH:16]2)=[O:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1429382,4-DichlorophenethylamineHCID 685123251-(2-cyano-4-(2-methoxy-2-oxoethyl)phenyl)-1H-indole-5-carboxylic acid

Product 1

HCID 68508412methyl 2-(4-(5-((2,4-dichlorophenethyl)carbamoyl)-1H-indol-1-yl)-3-cyanophenyl)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(2-cyano-4-(2-methoxy-2-oxoethyl)phenyl)-1H-indole-5-carboxylic acid (0.020 g, 0.078 mmol, triethylamine (0.013 mL, 0.090 mmol) and oxalyl chloride (0.010 g, 0.079 mmol) was combined in 1 mL of DCM and 1 drop of DMF was added. The reaction mixture was stirred at ambient temperature for 30 minutes. To the reaction mixture was added 2-(2,4-dichlorophenyl)ethanamine.The reaction mixture was stirred for 1 hour then loaded onto a silica gel column. The product was eluted with solvent system of 5% EtOAc/Hexanes to 100% EtOAc to provide methyl 2-(4-(5-((2,4-dichlorophenethyl)carbamoyl)-1H-indol-1-yl)-3-cyanophenyl)acetate (0.170 g, 0.034 mmol). MS(APCI)=506.1 (M+1).

Workup

  1. stirringThe reaction mixture was stirred for 1 hour
  2. washThe product was eluted with solvent system of 5% EtOAc/Hexanes to 100% EtOAc

Sources & evidence

ORD record
ord-db7791a83d7c4da681cc5bd1517e6739
Source dataset
uspto-grants-2013_01
Patent number
US08362056B2

Reaction notes

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