Methyl 2-(2-chloroethoxy)-4-methoxybenzoate → 2-(2-{4-[1-(2-ethoxyethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidin-1-yl}-ethoxy)-4-methoxy-benzoic acid methyl ester

HRID 1437186Notes

Reaction equation

HRID 1437186 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8](N2CCCCC2)=[CH:7]1)[CH3:2].[CH3:21][O:22][C:23](=[O:36])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1[O:32][CH2:33][CH2:34]Cl>>[CH3:21][O:22][C:23](=[O:36])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1[O:32][CH2:33][CH2:34][N:11]1[CH2:12][CH2:13][CH:14]([C:8]2[C:9]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[CH:7]=2)[CH2:9][CH2:10]1

Participants

3

Reactant 2

HCID 14087529Methyl 2-(2-chloroethoxy)-4-methoxybenzoateHCID 688947821-(2-ethoxyethyl)-3-piperidinyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 688938672-(2-{4-[1-(2-ethoxyethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidin-1-yl}-ethoxy)-4-methoxy-benzoic acid methyl esterYield 87.6%

Procedure

This compound was prepared following the procedure described in example 4, part E, starting with 3 g (10.9 mmol) of 1-(2-ethoxyethyl)-3-piperidin yl-1H-pyrrolo[2,3-b]pyridine and 4 g (16.5 mmol) of 2-(2-chloroethoxy)-4-methoxy-benzoic acid methyl ester. After standard work-up and purification, 2.3 g (44% yield) of 2-(2-{4-[1-(2-ethoxyethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidin-1-yl}-ethoxy)-4-methoxy-benzoic acid methyl ester were obtained.

Workup

  1. customThis compound was prepared
  2. customAfter standard work-up and purification

Sources & evidence

ORD record
ord-011d15d04afd4a808b8dd148e842f5cb
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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