Potassium Fluoride → N-[4-methyl-5-(3-thienyl)-1,3-thiazol-2-yl]acetamide

HRID 1360872Notes

Reaction equation

I[C:2]1[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][C:3]=1[CH3:11].[F-].[K+].CC1(C)C(C)(C)OB([C:22]2[CH:26]=[CH:25][S:24][CH:23]=2)O1>C1(C)C=CC=CC=1.CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:11][C:3]1[N:4]=[C:5]([NH:7][C:8](=[O:10])[CH3:9])[S:6][C:2]=1[C:22]1[CH:26]=[CH:25][S:24][CH:23]=1

Participants

Conditions

Temperature: 120 °C

Procedure

In a microwave tube, N-(5-iodo-4-methyl-1,3-thiazol-2-yl)acetamide, Intermediate 1 (564.2 mg; 2 mmol; 1 eq) and Pd(dppf)Cl2 (73.2 mg; 0.10 mmol; 0.05 eq) are suspended in Toluene (7 ml). A solution of potassium fluoride (464.8 mg; 8 mmol; 4 eq) in MeOH (7 ml) is added. 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene (630.3 mg; 3 mmol; 1.50 eq) is finally added as a solid. The resulting solution is flushed with argon, the tube is closed and heated under microwave action at 120° C. for 15 minutes. The reaction mixture is filtered over Celite and the solvents are evaporated. The resulting crude product is dissolved in EtOAc, washed with water and brine and dried over MgSO4. It is then purified by preparative HPLC, affording the title compound as white-off solid (316.7 mg; 66% yield).

Workup

customThe resulting solution is flushed with argon
customthe tube is closed
filtrationThe reaction mixture is filtered over Celite
customthe solvents are evaporated
dissolutionThe resulting crude product is dissolved in EtOAc
washwashed with water and brine
dry with materialdried over MgSO4
customIt is then purified by preparative HPLC

Sources & evidence

ORD record: ord-ccf3eacb5e914cfc8305ec894d642762
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879888B2

Reaction notes

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