Dichloromethane → HCID 66728362, compound

HRID 2097670Notes

Reaction equation

HRID 2097670 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]2[C:3]=1C=C[NH:6]2.[Al+3].[Cl-].[Cl-].[Cl-].Cl[C:20]([C:22]([CH2:24][CH3:25])=[O:23])=[O:21].[C:26]([O-:29])(O)=O.[Na+].[CH2:31](Cl)Cl>>[C:12]([NH:11][C:8]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]2[C:7]=1[NH:6][CH:25]=[C:24]2[C:22](=[O:23])[C:20]([O:29][CH2:26][CH3:31])=[O:21])(=[O:14])[CH3:13]

Participants

6

Reactant 5

HCID 6344Dichloromethane2×HCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) Chloride2×HCID 11007880Butanoyl chloride, 2-oxo-HCID 66728479N-(4-Fluoro-1H-indol-7-yl)acetamide

Product 1

HCID 66728362HCID 66728362, compound

Procedure

N-(4-fluoro-1H-indol-7-yl)acetamide (1 eq.) was added to a suspension of AlCl3 (1 eq.) in CH2Cl2 (100 ml). After 15 min, a premixed suspension of AlCl3 (2 eq.) and ClCOCOEt (2 eq.) in CH2Cl2 was added and stirring was continued at room temperature for 1 hour before iced saturated NaHCO3 solution was added. 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 ethyl 2-(7-acetamido-4-fluoro-1H-indol-3-yl)-2-oxoacetate. MS m/z: (M+H)+ calc'd for C14H14FN2O4:293.09. Found 293.11. HPLC retention time: 0.98 minutes (column E, solvent system II). 1H NMR (300 MHz, CD3OD) 8.32 (s, 1H), 7.16 (m, 1H), 6.94 (m, 1H), 4.43 (q, 2H, J=7.2 Hz), 2.24 (s, 3H), 1.39 (t, 3H, J=7.2 Hz).

Workup

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

Sources & evidence

ORD record
ord-bf2e4f71ba1f4212a447961092e16718
Source dataset
uspto-grants-2013_05
Patent number
US08450361B2

Reaction notes

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