Dimethylamine → HCID 68568190, compound

HRID 220621Notes

Reaction equation

HRID 220621 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7](C(OC(C)(C)C)=O)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[CH2:16]Br)=[O:5].[CH3:25][NH:26][CH3:27]>C1COCC1>[CH2:2]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[CH2:16][N:26]([CH3:27])[CH3:25])=[O:5])[CH3:1]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 67414524HCID 67414524, compound

Product 1

HCID 68568190HCID 68568190, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.200 g (0.48 mmol) of 7-bromomethyl-5-chloro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (previously described) in THF (3 ml) at RT, 0.17 ml of dimethyl amine (5.6 M in EtOH) was added. The reaction mixture was stirred at RT for one hour and concentrated under vacuo. The crude was dissolved in CH2Cl2 (1 m) and at RT 0.2 ml of TFA was added and stirring was continued over night. Preparative HPLC (30% CH3CN/H2O) afforded 67 mg (50%) of 5-chloro-7-dimethylaminomethyl-1H-indole-2-carboxylic acid ethyl ester as colorless oil. ES-MS m/e (%): 281.3 (M+H+).

Workup

  1. customat RT
  2. concentrationconcentrated under vacuo
  3. dissolutionThe crude was dissolved in CH2Cl2 (1 m) and at RT 0.2 ml of TFA
  4. additionwas added
  5. stirringstirring
  6. waitwas continued over night

Sources & evidence

ORD record
ord-e2f3e0ef5f174931b4fef0eb97a64855
Source dataset
uspto-grants-2012_06
Patent number
US08202993B2

Reaction notes

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