Trichloroacetyl chloride → HCID 21914140, compound

HRID 887920Notes

Reaction equation

HRID 887920 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:14]([NH2:16])=O)(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(Cl)(Cl)C(Cl)=O>C(Cl)Cl>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:14]#[N:16])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 21914123HCID 21914123, compound

Product 1

HCID 21914140HCID 21914140, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of intermediate (18) (0.0076 mole) in DCM (30 ml), cooled in an ice bath under argon, was added triethylamine (0.0228 mole) followed by trichloroacetyl chloride (0.0115 mole). The mixture was allowed to warm to room temperature and stir for 2 hours. The mixture was washed with water, 2N HCl, and saturated NaHCO3. The organic layer was dried and concentrated. The concentrate was triturated in ether and purified on silica gel column, eluting with 50% ethyl acetate in hexane. The desired fractions were combined and concentrated. The residue was triturated in ether and the solid collected by filtration and allowed to dry, yielding 0.30 g of 1-acetyl-5-fluoro-2,3-dihydro-1H-indole-2-carbonitrile (intermediate 19, mp. 93-95° C.).

Workup

  1. temperaturecooled in an ice bath under argon
  2. washThe mixture was washed with water, 2N HCl, and saturated NaHCO3
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customThe concentrate was triturated in ether
  6. custompurified on silica gel column
  7. washeluting with 50% ethyl acetate in hexane
  8. concentrationconcentrated
  9. customThe residue was triturated in ether
  10. filtrationthe solid collected by filtration
  11. customto dry

Sources & evidence

ORD record
ord-d9009f10378949acb219195c18fab2f2
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

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