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

HRID 1437197Notes

Reaction equation

HRID 1437197 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[CH:14][CH:15]=[C:10]3[C:9]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:8]2)=[CH:2]1.[CH3:22][O:23][C:24](=[O:37])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[O:33][CH2:34][CH2:35]Cl>>[CH3:22][O:23][C:24](=[O:37])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[O:33][CH2:34][CH2:35][N:19]1[CH2:18][CH2:17][CH:16]([C:9]2[C:10]3[C:11](=[CH:12][N:13]=[CH:14][CH:15]=3)[N:7]([CH2:6][C:3]3[CH:4]=[CH:5][O:1][CH:2]=3)[CH:8]=2)[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 14087529Methyl 2-(2-chloroethoxy)-4-methoxybenzoateHCID 179730281-furan-3-ylmethyl-3-piperidin-4-yl-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 688947762-{2-[4-(1-furan-3-ylmethyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-piperidin-1-yl]-ethoxy}-4-methoxy-benzoic acid methyl esterYield 37%

Procedure

This compound was prepared following the procedure described in example 4, part E, starting with 1.50 g (5.25 mmol) of 1-furan-3-ylmethyl-3-piperidin-4-yl-1H-pyrrolo[2,3-c]pyridine and 1.55 g (6.3 mmol) of 2-(2-chloroethoxy)-4-methoxybenzoic acid methyl ester. After standard work-up and purification, 0.95 g (36% yield) of 2-{2-[4-(1-furan-3-ylmethyl-1H-pyrrolo[2,3-c]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-b2b8920a268346c3a3b86d5b036ddfee
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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