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

HRID 887924Notes

Reaction equation

HRID 887924 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-41ce0dec3cd841d5a70dba407c222fed
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

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