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

HRID 1948413
Notes
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Reaction equation

HRID 1948413 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].CC1N=C(NC(=O)C)SC=1[C:18]1[S:19][C:20](S(NCC#C)(=O)=O)=[CH:21][CH:22]=1.[F-].[K+].CC1(C)C(C)(C)OB(C2C=CSC=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:21]=[CH:20][S:19][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 522689Potassium FluorideHCID 27605974,4,5,5-Tetramethyl-2-(thiophen-3-yl)-1,3,2-dioxaborolaneHCID 11998301N-(4-methyl-5-{5-[(prop-2-yn-1-ylamino)sulfonyl]-2-thienyl}-1,3-thiazol-2-yl)acetamideHCID 57417074N-(5-Iodo-4-methyl-2-thiazolyl)acetamide

Product 1

HCID 11993592N-[4-methyl-5-(3-thienyl)-1,3-thiazol-2-yl]acetamideYield 66%

Reagents, catalysts & solvents 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

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

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

Sources & evidence

ORD record
ord-01b342f608534d1abbdd369d629f2a8a
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399497B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes