Dimethylformamide → HCID 68264841, compound

HRID 877484Notes

Reaction equation

HRID 877484 reaction equation
[Cl:1][C:2]1[C:10]2[NH:9][C:8]3[C:11](=[O:14])[CH2:12][CH2:13][C:7]=3[C:6]=2[CH:5]=[C:4]([Cl:15])[CH:3]=1.[C:16]([O-:19])([O-])=O.[K+].[K+].CN([CH:25]=[O:26])C>O>[C:16]([O:26][CH2:25][N:9]1[C:10]2[C:2]([Cl:1])=[CH:3][C:4]([Cl:15])=[CH:5][C:6]=2[C:7]2[CH2:13][CH2:12][C:11](=[O:14])[C:8]1=2)(=[O:19])[C:6]([CH3:7])([CH3:10])[CH3:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 68264843HCID 68264843, compound

Product 1

HCID 68264841HCID 68264841, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5,7-dichloro-1,2-dihydrocyclopenta[b]indol-3(4H)-one (0.1 g, 0.41 mmol) in anhydrous DMF (5 mL), K2CO3 (80 mg, 0.62 mmol) was added followed by chloro methyl pivalate (0.07 mL, 0.51 mmol) and the resulting mixture stirred at room temperature for 3 h. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude compound which was purified by silica gel chromatography [EtOAc-hexane (3:17) as eluant] to provide the title compound as a yellow solid (0.10 g, 68%). 1H NMR (500 MHz, CDCl3, δ in ppm) 7.61 (s, 1H), 7.41 (s, 1H), 6.56 (s, 2H), 3.04 (s, 4H), 1.14 (s, 9H).

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto give the crude compound which
  5. customwas purified by silica gel chromatography [EtOAc-hexane (3:17) as eluant]

Sources & evidence

ORD record
ord-ac47ac7864b8471fbd81ff837ad26ae2
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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