2-Mercaptobenzoic Acid → Ethyl 2-(4-acetamido-2-methyl-1H-indol-1-yl)acetate

HRID 2246711Notes

Reaction equation

HRID 2246711 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1C(=CC=CC=1)S.[C:11]([NH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17](SC1C=CC(Cl)=CC=1)[C:18]([CH3:28])(CC(O)=O)[NH:19]2)(=[O:13])[CH3:12].F[C:38](F)(F)[C:39](O)=O>>[C:11]([NH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17]=[C:18]([CH3:28])[N:19]2[CH2:2][C:1]([O:10][CH2:38][CH3:39])=[O:9])(=[O:13])[CH3:12]

Participants

4

Reactant 3

HCID 54432-Mercaptobenzoic Acid2×HCID 6422Trifluoroacetic acidHCID 669653494-(acetylamino)-3-[(4-chlorophenyl)thio]-2-methyl-1H-indole-acetic acid

Product 1

HCID 59431286Ethyl 2-(4-acetamido-2-methyl-1H-indol-1-yl)acetate

Conditions

Temperature
60 °C

Procedure

Thiosalicylic acid was added to a solution of the product from Example 1 part (iv) (474 mg) in trifluoroacetic acid (10 ml) was added thiosalicylic acid (351 mg) and the resulting suspension was heated to 60° C. for 4 hours. The mixture was concentrated in vacuo and the residue dissolved in EtOAc and washed with NaHCO3 (aq), brine, dried (MgSO4) and evaporated to give crude material. Purification by column chromatography (50% EtOAc/hexane as eluent) gave the sub-title compound (0.13 g).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in EtOAc
  3. washwashed with NaHCO3 (aq), brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give crude material
  7. customPurification by column chromatography (50% EtOAc/hexane as eluent)

Sources & evidence

ORD record
ord-f0a0cca00f984f35a7fdf98d11e93854
Source dataset
uspto-grants-2010_03
Patent number
US07687535B2

Reaction notes

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