4'-Fluoro-2'-nitroacetanilide → N-(4-Fluoro-1H-indol-7-yl)acetamide

HRID 2097669Notes

Reaction equation

HRID 2097669 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[N+:12]([O-])=O)=[O:3].[CH:15]([Mg]Br)=[CH2:16]>C1COCC1>[F:11][C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:2](=[O:3])[CH3:1])=[C:6]2[C:7]=1[CH:15]=[CH:16][NH:12]2

Participants

4

Reactant 2

HCID 1362894'-Fluoro-2'-nitroacetanilideHCID 178418507HCID 178418507, compound

Product 1

HCID 66728479N-(4-Fluoro-1H-indol-7-yl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-Fluoro-2-nitroacetanilide (1 eq.) was dissolved in dry THF. After the solution was cooled down to −78° C., an excess of vinyl magnesium bromide (3-4 eq.) was added. Then, the reaction was kept below −40° C. for two hours before quenched with 20% NH4Cl. The aqueous phase was extracted with EtOAc. The combined organic layer was dried over MgSO4. After filtration and concentration, the crude product was purified by silica gel column chromatography to afford N-(4-fluoro-1H-indol-7-yl)acetamide. MS m/z: (M+H)+ calc'd for C10H10FN2O: 193.08. Found 193.09. HPLC retention time: 1.29 minutes (column E, solvent system II).

Workup

  1. custombefore quenched with 20% NH4Cl
  2. extractionThe aqueous phase was extracted with EtOAc
  3. dry with materialThe combined organic layer was dried over MgSO4
  4. filtrationAfter filtration and concentration
  5. customthe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-24eb95aa675240619a3f3576545f7b59
Source dataset
uspto-grants-2013_05
Patent number
US08450361B2

Reaction notes

Loading…