Water → 6-Cyano-2-methyl-4H-thieno[3,2-b]pyrrole
Reaction equation
[C:1]([C:3]1[C:4]2[S:13][C:12]([CH3:14])=[CH:11][C:5]=2[NH:6][C:7]=1C(O)=O)#[N:2].O>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[C:1]([C:3]1[C:4]2[S:13][C:12]([CH3:14])=[CH:11][C:5]=2[NH:6][CH:7]=1)#[N:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 200 °C
Procedure
To a solution of 6-cyano-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylic acid (0.54 g) in quinoline (10 mL) was added Copper powder (33 mg), and the mixture was stirred at 200° C. for 30 minutes using microwave reactor. To the reaction solution was added water, and a precipitated insoluble matter was filtered through a Celite pad (registered trademark). The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with 1 mol/L hydrochloric acid, water and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=76/24−53/47) to give the title compound (0.37 g).
Workup
- filtrationa precipitated insoluble matter was filtered through a Celite pad (registered trademark)
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with ethyl acetate
- washThe combined organic layer was washed with 1 mol/L hydrochloric acid, water and brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe obtained residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=76/24−53/47)
Sources & evidence
- ORD record
- ord-11721788f7a745bfb04b3ff266d74a88
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115144B2
Reaction notes
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