Quinoline → HCID 58425691, compound

HRID 2173041Notes

Reaction equation

HRID 2173041 reaction equation
[CH3:1][N:2]1[C:6]2[S:7][C:8](C(O)=O)=[CH:9][C:5]=2[C:4]([CH3:13])=[N:3]1.N1C2C(=CC=CC=2)C=CC=1>[Cu]>[CH3:1][N:2]1[C:6]2[S:7][CH:8]=[CH:9][C:5]=2[C:4]([CH3:13])=[N:3]1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 27765411,3-dimethyl-1H-thieno[2,3-c]pyrazole-5-carboxylic acid

Product 1

HCID 58425691HCID 58425691, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
200 °C

Procedure

A mixture of 1,3-dimethyl-1H-thieno[2,3-c]pyrazole-5-carboxylic acid (2 g, 10.19 mmol), copper (1.943 g, 30.6 mmol) and quinoline (10 mL, 85 mmol) were heated to 200° C. for 1 hour in a Biotage Initiator microwave. Following heating, the mixture was extracted with ethyl acetate (3×100 mL) and 3N HCl (200 mL). The organic layers were combined, dried over sodium sulfate, concentrated, and purified via silica gel flash chromatography, eluting with a gradient of 10-40% EtOAc and hexane to give the title compound as a clear oil (1.07 g, 69%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.32 (s, 9H), 3.83 (s, 3H), 6.98 (d, J=5.40 Hz, 1H), 7.09 (d, J=4.90 Hz, 1H). ESI-MS m/z [M+H]+ calc'd for C7H8N2S, 153. found, 153.

Workup

  1. temperatureFollowing heating
  2. extractionthe mixture was extracted with ethyl acetate (3×100 mL) and 3N HCl (200 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified via silica gel flash chromatography
  6. washeluting with a gradient of 10-40% EtOAc and hexane

Sources & evidence

ORD record
ord-066f57c09dda47ee81faf63d22a3bd6f
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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