Potassium Phosphate, Tribasic → Ethyl 6-cyano-2,3-dimethyl-4H-thieno[3,2-b]pyrrole-5-carboxylate

HRID 518128Notes

Reaction equation

Br[C:2]1[C:6]2[NH:7][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([C:10]#[N:11])[C:5]=2[S:4][C:3]=1[CH3:17].[CH3:18]B1OB(C)OB(C)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:10]([C:9]1[C:5]2[S:4][C:3]([CH3:17])=[C:2]([CH3:18])[C:6]=2[NH:7][C:8]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:11]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of ethyl 3-bromo-6-cyano-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate (0.2 g) in 1,4-dioxane (4.0 mL) were added 2,4,6-trimethylboroxine (0.64 g), copper(I) iodide (50 mg), tripotassium phosphate (0.27 g) and tetrakis(triphenylphosphine)palladium (0.22 g), and the mixture was stirred at 150° C. for 150 minutes using microwave reactor. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=76/24−55/45) to give the title compound (0.13 g).

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customthe obtained residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=76/24−55/45)

Sources & evidence

ORD record: ord-7594dd0c2c0a4376bc44e972dbd7e33b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115144B2

Reaction notes

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