Dimethylamine → 6-Bromo-1-cyanomethyl-1H-indole-3-carboxylic Acid Dimethylamide

HRID 23415Notes

Reaction equation

HRID 23415 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:14]([OH:16])=O)=[CH:7][N:8]2[CH2:11][C:12]#[N:13])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:23][NH:24][CH3:25].O>ClC(Cl)C.CN(C=O)C>[CH3:23][N:24]([CH3:25])[C:14]([C:6]1[C:5]2[C:9](=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=2)[N:8]([CH2:11][C:12]#[N:13])[CH:7]=1)=[O:16]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 65578Oxalyl chlorideHCID 225740826-Bromo-1-cyanomethyl-1H-indole-3-carboxylic Acid

Product 1

HCID 695459176-Bromo-1-cyanomethyl-1H-indole-3-carboxylic Acid DimethylamideYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

To a suspension of 6-bromo-1-cyanomethyl-1H-indole-3-carboxylic acid (0.478 g, 1.71 mmole) in dichloroethane (100 ml) was added oxalyl chloride (2.6 g, 20.55 mmole) at room temperature followed by a few drops of anhydrous DMF. The reaction was stirred at the same temperature for 24 h. To this mixture was added dimethyl amine (21.4 ml, 2 N in THF, 42.8 mmole) slowly. The reaction mixture was then poured into water (200 ml) and the organic phase was separated, evaporated to dryness and the residue was purified by column chromatography (silica gel, hexane:ethyl acetate 1:1). The pure product weighed 0.335 g (63% yield).

Workup

  1. customthe organic phase was separated
  2. customevaporated to dryness
  3. customthe residue was purified by column chromatography (silica gel, hexane:ethyl acetate 1:1)

Sources & evidence

ORD record
ord-d37802f99ae04993bd910c59c5da758e
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Reaction notes

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