Ethyl bromoacetate → (5-{3-[(2-Chloro-5-methyl-pyrimidin-4-yl)-methyl-amino]-propoxy}-indol-1-yl)-acetic acid ethyl ester

HRID 734448Notes

Reaction equation

HRID 734448 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[CH:17]3)[CH3:9])[C:5]([CH3:23])=[CH:4][N:3]=1.[H-].[Na+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CN(C=O)C.O>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][N:19]1[C:20]2[C:16](=[CH:15][C:14]([O:13][CH2:12][CH2:11][CH2:10][N:8]([C:6]3[C:5]([CH3:23])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH3:9])=[CH:22][CH:21]=2)[CH:17]=[CH:18]1)[CH3:32]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 57845512(2-chloro-5-methyl-pyrimidin-4-yl)-[3-(1H-indol-5-yloxy)-propyl]-methyl-amine

Product 1

HCID 57845454(5-{3-[(2-Chloro-5-methyl-pyrimidin-4-yl)-methyl-amino]-propoxy}-indol-1-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(2-Chloro-5-methyl-pyrimidin-4-yl)-[3-(1H-indol-5-yloxy)-propyl]-methyl-amine (Example 88, 0.117 g, 0.35 mmol) was dissolved in DMF (2 mL) at rt, and sodium hydride was added (0.017 g, 60% in mineral oil, 0.42 mmol). The reaction solution immediately turned purple. The resulting mixture was stirred for 1 h and ethyl bromoacetate (0.065 g, 0.39 mmol) was added. The reaction mixture was stirred for 60 h, diluted with water, and extracted with EtOAc. The organic phases were dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound as an orange oil without purification (103 mg, 70%). LC/MS m/z 417.4 (M+H)+, RT 3.05 min.

Workup

  1. stirringThe reaction mixture was stirred for 60 h
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5efeb0b956d24541aa8e7e82810b746a
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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