Hydrogen Sulfide → methyl (5-{3-[4-(aminocarbonothioyl)-2-propylphenoxy]-propoxy}-1H-indol-1-yl)acetate

HRID 734418Notes

Reaction equation

[SH2:1].[C:2]([C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:17]=[CH:16]3)=[C:6]([CH2:29][CH2:30][CH3:31])[CH:5]=1)#[N:3].C(NCC)C>CN(C=O)C>[NH2:3][C:2]([C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:17]=[CH:16]3)=[C:6]([CH2:29][CH2:30][CH3:31])[CH:5]=1)=[S:1]

Participants

Conditions

Temperature: 70 °C

Procedure

Hydrogen sulfide was passed through a solution of methyl {5-[3-(4-cyano-2-propylphenoxy)propoxy]-1H-indol-1-yl}acetate (Example 51, 787 mg, 1.94 mmol) in DMF (15 mL) for 30 minutes at rt. Diethyl amine (0.3 mL, 2.90 mmol) was added, and the solution was heated to 70° C. for 3 h. The reaction mixture was cooled to rt, and the residual H2S was removed by passing argon through the reaction mixture for 30 minutes. The solvent was evaporated under reduced pressure and the residue was filtered through a plug of silica and washed with EtOAc. Concentration of solvent yielded a brown oil which was used in the next step without further purification. LC/MS m/z 441.2 (M+H)+; RT 3.35 min.

Workup

temperatureThe reaction mixture was cooled to rt
customthe residual H2S was removed
customfor 30 minutes
customThe solvent was evaporated under reduced pressure
filtrationthe residue was filtered through a plug of silica
washwashed with EtOAc
customConcentration of solvent yielded a brown oil which
customwas used in the next step without further purification
customRT 3.35 min.

Sources & evidence

ORD record: ord-55255b986b944a3d92e37d5b0e558f0d
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592361B2

Reaction notes

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