Trichloroacetyl chloride → 1-acetyl-2,3-dihydro-5-methoxy-1H-indole-2-carbonitrile

HRID 1246204Notes

Reaction equation

HRID 1246204 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:15]([NH2:17])=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]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:15]#[N:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 219141281-acetyl-2,3-dihydro-5-methoxy-1H-indole-2-carboxamide

Product 1

HCID 219141141-acetyl-2,3-dihydro-5-methoxy-1H-indole-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of intermediate (22) (0.022 mole) in DCM (150 ml), cooled in an ice bath under argon, was added triethylamine (0.066 mole) then trichloroacetyl chloride (0.033 mole). The mixture was allowed to slowly warmed to room temperature overnight. The mixture was washed with water, 2N HCl, and saturated NaHCO3. The organic phase was dried, concentrated and triturated in ether and the solid collected, yielding 1-acetyl-2,3-dihydro-5-methoxy-1H-indole-2-carbonitrile (intermediate 23, mp. 108–110° 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 phase was dried
  4. concentrationconcentrated
  5. customtriturated in ether
  6. customthe solid collected

Sources & evidence

ORD record
ord-0319c440934c47e994aa1fddc094a80f
Source dataset
uspto-grants-2006_10
Patent number
US07125891B2

Reaction notes

Loading…