HCID 178418546, compound → HCID 178509424, compound

HRID 2299291Notes

Reaction equation

HRID 2299291 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:20])=[C:12]3[CH:18]=[C:17](I)[S:16][C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[C:23]([Cu])#[N:24]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:20])=[C:12]3[CH:18]=[C:17]([C:23]#[N:24])[S:16][C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 178418546HCID 178418546, compoundHCID 178522942HCID 178522942, compound

Product 1

HCID 178509424HCID 178509424, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-(4-chlorobenzyl)4-hydroxy-2-iodothieno[2,3-b]pyridine-5-carboxamide (Example No. 2) (0.500 g) in pyridine (5 mL) is added CuCN (0.201 g). The reaction is heated to reflux and stirred for 18 h. The reaction mixture is purified via column chromatography (CH2Cl2:CH3OH; 98:2). Fractions homogeneous by TLC are combined and concentrated in vacuo to yield a pale yellow solid which is recrystallized from methanol to yield 0.100 g (26%) of the title compound as an off-white solid.

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux
  3. customThe reaction mixture is purified via column chromatography (CH2Cl2:CH3OH; 98:2)
  4. concentrationconcentrated in vacuo
  5. customto yield a pale yellow solid which
  6. customis recrystallized from methanol

Sources & evidence

ORD record
ord-a86b212d0e284369ac1e555f8ff76235
Source dataset
uspto-grants-2002_12
Patent number
US06495683B2

Reaction notes

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