Morpholine → HCID 67414308, compound

HRID 220617Notes

Reaction equation

HRID 220617 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-d1d22b3d78984d1eb6ac7b6b2e1fd654
Source dataset
uspto-grants-2012_06
Patent number
US08202993B2

Reaction notes

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