Methyl 2-(2-chloroethoxy)benzoate → 2-(2-{4-[1-(5-chlorothiophen-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl}ethoxy)benzoic acid methyl ester

HRID 1437179Notes

Reaction equation

HRID 1437179 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:9]2)=[CH:4][CH:3]=1.Cl[CH2:24][CH2:25][O:26][C:27]1[CH:36]=[CH:35][CH:34]=[CH:33][C:28]=1[C:29]([O:31][CH3:32])=[O:30]>>[CH3:32][O:31][C:29](=[O:30])[C:28]1[CH:33]=[CH:34][CH:35]=[CH:36][C:27]=1[O:26][CH2:25][CH2:24][N:20]1[CH2:19][CH2:18][CH:17]([C:10]2[C:11]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:8]([CH2:7][C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:9]=2)[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 9837283Methyl 2-(2-chloroethoxy)benzoateHCID 179729751-(5-chlorothiophen-2-ylmethyl)3-piperidin-4-yl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 688943472-(2-{4-[1-(5-chlorothiophen-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl}ethoxy)benzoic acid methyl esterYield 33.2%

Procedure

This compound was prepared following the procedure described in example 4, part E starting with 2.8 g (6.5 mmol) of 1-(5-chloro-thiophen-2-ylmethyl)3-piperidin-4-yl-1H-pyrrolo[2,3-b]pyridine and 1.5 g (7.2 mmol) of methyl 2-(2-chloroethoxy)benzoate. After standard work-up and purification, 1.1 g (33% yield) of 2-(2-{4-[1-(5-chlorothiophen-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl}ethoxy)benzoic acid methyl ester were obtained.

Workup

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

Sources & evidence

ORD record
ord-26b3d2e02d634efea25c520ee475a566
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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