2-[4-[2-(1-Pyrrolidinyl)ethoxy)phenyl]benzo[b]thiophene → 3-Methoxy-4-[(1-pyrrolidinyl)methyl]phenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl Ketone

HRID 1387074Notes

Reaction equation

HRID 1387074 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:6]([O:8]C)=O.[S:19]1[C:23]([C:24]2[CH:37]=[CH:36][C:27]([O:28][CH2:29][CH2:30][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:26][CH:25]=2)=[CH:22][C:21]2[CH:38]=[CH:39][CH:40]=[CH:41][C:20]1=2>>[N:31]1([CH2:30][CH2:29][O:28][C:27]2[CH:36]=[CH:37][C:24]([C:23]3[S:19][C:20]4[CH:41]=[CH:40][CH:39]=[CH:38][C:21]=4[C:22]=3[C:6]([C:5]3[CH:10]=[CH:11][C:12]([CH2:13][N:14]4[CH2:18][CH2:17][CH2:16][CH2:15]4)=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:8])=[CH:25][CH:26]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 106637082-[4-[2-(1-Pyrrolidinyl)ethoxy)phenyl]benzo[b]thiopheneHCID 10824510Methyl 3-methoxy-4-(pyrrolidin-1-ylmethyl)benzoate

Product 1

HCID 206668513-Methoxy-4-[(1-pyrrolidinyl)methyl]phenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl KetoneYield 51%

Procedure

By essentially following the procedure used to prepare Example 137, Part C, the title compound was prepared from methyl 3-methoxy-4-[(1-pyrrolidinyl)methyl]benzoate (Part B) and 1-[2-[4-(benzo[b]thiophen-2-yl)phenoxy]ethyl]pyrrolidine (Example 4, Part A) in 51% yield as a yellow foam. The flash chromatography was carried out by eluting with a gradient of EtOAc(100-90%)/Et3N(0-5%)/MeOH(0-5%).

Workup

  1. customto prepare Example 137, Part C
  2. washby eluting with a gradient of EtOAc(100-90%)/Et3N(0-5%)/MeOH(0-5%)

Sources & evidence

ORD record
ord-a5aa2de8806847ee9ad11f6dea0aa646
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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