Potassium Carbonate → Methyl 4-(6-cyano-2-methyl-thieno[3,2-b]pyrrol-4-yl)-2-(methoxymethoxy)benzoate

HRID 518131Notes

Reaction equation

[C:1]([C:3]1[C:4]2[S:10][C:9]([CH3:11])=[CH:8][C:5]=2[NH:6][CH:7]=1)#[N:2].I[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:23][CH2:24][O:25][CH3:26])[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[C:1]([C:3]1[C:4]2[S:10][C:9]([CH3:11])=[CH:8][C:5]=2[N:6]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:23][CH2:24][O:25][CH3:26])[CH:14]=2)[CH:7]=1)#[N:2]

Participants

Conditions

Temperature: 170 °C

Procedure

To a solution of 6-cyano-2-methyl-4H-thieno[3,2-b]pyrrole (0.37 g) in toluene (10 mL) were added methyl 4-iodo-2-(methoxymethoxy)benzoate (0.73 g), copper(I) iodide (43 mg), trans-N,N′-dimethylcyclohexanediamine (65 mg) and potassium carbonate (0.66 g), and the mixture was stirred at 170° C. for 20 minutes using microwave reactor. The reaction solution was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=78/22−57/43) to give the title compound (0.63 g).

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=78/22−57/43)

Sources & evidence

ORD record: ord-9bfa7c8b3fbb48899c34e019bb4588d6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115144B2

Reaction notes

Loading…