Dimethylformamide dimethyl acetal → (E)-3-(dimethylamino)-1-(thieno[3,2-c]pyridin-2-yl)prop-2-en-1-one

HRID 1529467Notes

Reaction equation

CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[S:9]1[C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[CH:11]=[C:10]1[C:18](=[O:20])[CH3:19]>CN(C=O)C.CCOC(C)=O.O>[CH3:6][N:4]([CH3:5])/[CH:3]=[CH:19]/[C:18]([C:10]1[S:9][C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[CH:11]=1)=[O:20]

Participants

Conditions

Temperature: 70 °C

Procedure

N,N-dimethylformamide-dimethylacetal (DMF-DMA) (9.5 ml) was added to a solution of 1-(thieno[3,2-c]pyridin-2-yl)ethanone (3.17 g) in 20 mL DMF. The reaction was heated to 70° C. overnight. The reaction was then cooled to room temperature. The DMF was removed on a rotary evaporator to obtain a dark brown orange solid. The residue was diluted with EtOAc and water. A large amount of yellow solid was evident. This was collected by filtration (3.54 g). This solid was dried in a 50° C. vacuum oven.

Workup

temperatureThe reaction was then cooled to room temperature
customThe DMF was removed on a rotary evaporator
customto obtain a dark brown orange solid
filtrationThis was collected by filtration (3.54 g)
customThis solid was dried in a 50° C. vacuum oven

Sources & evidence

ORD record: ord-c5268cb21f484caf8e749e4dd532693a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090625B2

Reaction notes

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