Morpholine → HCID 67414308, compound

HRID 912751Notes

Reaction equation

HRID 912751 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].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>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:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:5])[CH3:1]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 67414524HCID 67414524, compound

Product 1

HCID 67414308HCID 67414308, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 0.11 g (0.26 mmol) of 7-bromomethyl-5-chloro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in THF (1 ml) at RT, 40 μl of morpholine was added. The reaction mixture was stirred at 40° C. 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 53 mg (62%) of 5-chloro-7-morpholin-4-ylmethyl-1H-indole-2-carboxylic acid ethyl ester as colorless oil.

Workup

  1. concentrationconcentrated under vacuo
  2. dissolutionThe crude was dissolved in CH2Cl2 (1 m) and at RT
  3. addition0.2 ml of TFA was added
  4. stirringstirring
  5. waitwas continued over night

Sources & evidence

ORD record
ord-aec4ea205a28497681dc7ecdeaa9346c
Source dataset
uspto-grants-2011_09
Patent number
US08026259B2

Reaction notes

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