2-Bromopyridine → 5-Chloro-N-{1,3-dioxo-2-[1-(2-pyridinyl)-4-piperidinyl]-2,3-dihydro-1H-isoindol-4-yl}-2-thiophenecarboxamide

HRID 457754Notes

Reaction equation

HRID 457754 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[C:12](=[O:26])[N:13]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[C:14]3=[O:19])=[O:8])=[CH:4][CH:3]=1.Br[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1>N1C=CC=CC=1>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[C:12](=[O:26])[N:13]([CH:20]2[CH2:25][CH2:24][N:23]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:22][CH2:21]2)[C:14]3=[O:19])=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 79732-BromopyridineHCID 120748935-chloro-N-[1,3-dioxo-2-(4-piperidinyl)-2,3-dihydro-1H-isoindol-4-yl]-2-thiophenecarboxamide

Product 1

HCID 184406815-Chloro-N-{1,3-dioxo-2-[1-(2-pyridinyl)-4-piperidinyl]-2,3-dihydro-1H-isoindol-4-yl}-2-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

100 mg (0.257 mmol) of 5-chloro-N-[1,3-dioxo-2-(4-piperidinyl)-2,3-dihydro-1H-isoindol-4-yl]-2-thiophenecarboxamide and 0.05 ml (0.513 mmol) of 2-bromopyridine in 0.5 ml of pyridine are stirred at 110° C. for 48 h. The mixture is concentrated and dried under high vacuum. The product is isolated by preparative RP-HPLC.

Workup

  1. concentrationThe mixture is concentrated
  2. customdried under high vacuum
  3. customThe product is isolated by preparative RP-HPLC

Sources & evidence

ORD record
ord-ff2066e1b2c144a4a3bb826b73362d75
Source dataset
uspto-grants-2007_03
Patent number
US07189738B2

Reaction notes

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