Acetyl chloride → HCID 11521901, compound

HRID 907126Notes

Reaction equation

HRID 907126 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:5]([CH2:18][CH3:19])[C:6]2[C:11]([C:12]=1[C:13]#[N:14])=[CH:10][CH:9]=[C:8]([N+:15]([O-:17])=[O:16])[CH:7]=2.[C:20](Cl)(=[O:22])[CH3:21]>O1CCOCC1>[C:13]([C:12]1[C:11]2[C:6](=[CH:7][C:8]([N+:15]([O-:17])=[O:16])=[CH:9][CH:10]=2)[N:5]([CH2:18][CH3:19])[C:4]=1[NH:3][C:20](=[O:22])[CH3:21])#[N:14]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 59425037HCID 59425037, compound

Product 1

HCID 11521901HCID 11521901, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Sodium hydride (44 mg, 1.10 mmol, 60% w/w in mineral oil) was washed with hexanes and suspended in 1,4-dioxane (3 mL). A solution of 2-amino-1-ethyl-6-nitro-1H-indole-3-carbonitrile (120 mg, 0.521 mmol), prepared in step B, above, in dioxane (2 mL) was added, and the resulting mixture was allowed to stir for 30 min. Then, acetyl chloride (45 μL, 0.63 mmol) was added by syringe, and the solution was stirred for an additional 12 h. The reaction was partitioned between water and EtOAc (20 mL each), and the organic phase was washed with brine. The aqueous phases were back-extracted in sequence with ethyl acetate, and the organic extracts were combined, dried over MgSO4, filtered and evaporated. The resulting solid was triturated with Et2O, collected by filtration and dried under vacuum to afford N-(3-cyano-1-ethyl-6-nitro-1H-indol-2-yl)-acetamide (100 mg, 71%), compound 25, as an off-white powder.

Workup

  1. stirringthe solution was stirred for an additional 12 h
  2. customThe reaction was partitioned between water and EtOAc (20 mL each)
  3. washthe organic phase was washed with brine
  4. extractionThe aqueous phases were back-extracted in sequence with ethyl acetate
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting solid was triturated with Et2O
  9. filtrationcollected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-e65d2f222d394fb081de1144602b9dd4
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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