HCID 86686482, compound → HCID 66764700, compound

HRID 1466887Notes

Reaction equation

HRID 1466887 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([S:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[CH:22]=[N:23]O)=[C:9]1[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OC(=O)C)(=O)C.CCOC(C)=O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([S:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]#[N:23])=[C:9]1[CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86686482HCID 86686482, compound

Product 1

HCID 66764700HCID 66764700, compound

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

3-(1-Benzyl-6-chloro-2-methyl-1H-indol-3-ylsulfanyl)-benzaldehyde oxime from the previous step was dissolved in acetic anhydride (0.500 mL) and the reaction was heated to 135° C. overnight. The reaction mixture was diluted with EtOAc then concentrated and purified by silica gel chromatography (0-50% EtOAc in hexanes) to give the title compound.

Workup

  1. concentrationthen concentrated
  2. custompurified by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-89f81005af6a4b06907d4263a63c3ec2
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

Loading…