Potassium Carbonate → 5-Cyano-3-amino-2-(2'-ethoxy-5'-fluorobenzoyl)-thieno[2,3-b]pyridine

HRID 450857Notes

Reaction equation

HRID 450857 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:11]=1[C:12](=[O:15])[CH2:13]Br)[CH3:8].[C:21]([C:23]1[C:24]([SH:31])=[N:25][CH:26]=[C:27]([C:29]#[N:30])[CH:28]=1)#[N:22]>CN(C=O)C.C(OCC)(=O)C>[C:29]([C:27]1[CH:28]=[C:23]2[C:21]([NH2:22])=[C:13]([C:12](=[O:15])[C:11]3[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:10]=3[O:9][CH2:7][CH3:8])[S:31][C:24]2=[N:25][CH:26]=1)#[N:30]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 587073552-Ethoxy-5-fluorophenacyl bromideHCID 178510368HCID 178510368, compound

Product 1

HCID 692826645-Cyano-3-amino-2-(2'-ethoxy-5'-fluorobenzoyl)-thieno[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of potassium carbonate (1.18 g, 8.55 mmol), 2-ethoxy-5-fluorophenacyl bromide (1.34 g, 5.12 mmol) and 3,5-dicyano-2-mercaptopyridine (0.55 g, 3.42 mmol) in dry DMF (8 ml) is stirred at room temperature for 16 h. The resulting mixture is diluted with ethyl acetate and washed with water. Drying over sodium sulfate, filtering, evaporating the solvent and purification of the residue by silicagel column chromatography yields the title compound, having a m.p. of 196° C.

Workup

  1. washwashed with water
  2. dry with materialDrying over sodium sulfate
  3. filtrationfiltering
  4. customevaporating
  5. customthe solvent and purification of the residue by silicagel column chromatography

Sources & evidence

ORD record
ord-1d997590e2a64ba6a96a8e4f543e8442
Source dataset
uspto-grants-2013_07
Patent number
US08486996B2

Reaction notes

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