Acetyl chloride → HCID 11521901, compound

HRID 252519Notes

Reaction equation

HRID 252519 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) is 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) is added, and the resulting mixture is allowed to stir for 30 min. Then, acetyl chloride (45 μL, 0.63 mmol) is added by syringe, and the solution is stirred for an additional 12 h. The reaction is partitioned between water and EtOAc (20 mL each), and the organic phase is washed with brine. The aqueous phases are back-extracted in sequence with ethyl acetate, and the organic extracts are combined, dried over MgSO4, filtered and evaporated. The resulting solid is 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 is stirred for an additional 12 h
  2. customThe reaction is partitioned between water and EtOAc (20 mL each)
  3. washthe organic phase is washed with brine
  4. extractionThe aqueous phases are back-extracted in sequence with ethyl acetate
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting solid is triturated with Et2O
  9. filtrationcollected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-a22d3b3160244b16ae78328d669a02e8
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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