Potassium Carbonate → 5,6-Dimethyl-3-amino-2-(2',5'-difluorobenzoyl)-thieno[2,3-b]pyridine

HRID 450856

Reaction equation

HRID 450856 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:9]=1[C:10](=[O:13])[CH2:11]Br.[CH3:19][C:20]1[C:21]([CH3:29])=[N:22][C:23]([SH:28])=[C:24]([CH:27]=1)[C:25]#[N:26]>CN(C=O)C.C(OCC)(=O)C>[CH3:19][C:20]1[CH:27]=[C:24]2[C:25]([NH2:26])=[C:11]([C:10](=[O:13])[C:9]3[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:8]=3[F:7])[S:28][C:23]2=[N:22][C:21]=1[CH3:29]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27782642-Bromo-1-(2,5-difluorophenyl)ethanoneHCID 178426634HCID 178426634, compound

Product 1

HCID 692802095,6-Dimethyl-3-amino-2-(2',5'-difluorobenzoyl)-thieno[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of potassium carbonate (0.399 g, 2.89 mmol), 2,5-difluorophenacyl bromide (0.408 g, 1.73 mmol) and 5,6-dimethyl-2-mercaptonicotine nitrile (0.19 g, 1.16 mmol) in dry DMF (4 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 with a m.p. of 188° 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-4feec454f3c245e1b30ef272160fd095
Source dataset
uspto-grants-2013_07
Patent number
US08486996B2

Linked notes

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