5,7-Dichloroindoline → 5-Chloro-3-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-1-[2-(methylthio)ethyl]-2(1H)-pyrazinone

HRID 1271175Notes

Reaction equation

HRID 1271175 reaction equation
Cl[C:2]1[C:3](=[O:13])[N:4]([CH2:9][CH2:10][S:11][CH3:12])[CH:5]=[C:6]([Cl:8])[N:7]=1.[Cl:14][C:15]1[CH:16]=[C:17]2[C:21](=[C:22]([Cl:24])[CH:23]=1)[NH:20][CH2:19][CH2:18]2>>[Cl:8][C:6]1[N:7]=[C:2]([N:20]2[C:21]3[C:17](=[CH:16][C:15]([Cl:14])=[CH:23][C:22]=3[Cl:24])[CH2:18][CH2:19]2)[C:3](=[O:13])[N:4]([CH2:9][CH2:10][S:11][CH3:12])[CH:5]=1

Participants

3

Reactant 2

HCID 124822955,7-DichloroindolineHCID 184528023,5-dichloro-1-[2-(methylthio)ethyl]-2(1H)-pyrazinone

Product 1

HCID 101350185-Chloro-3-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-1-[2-(methylthio)ethyl]-2(1H)-pyrazinone

Procedure

Prepared in a similar fashion as described for Example 413 using 3,5-dichloro-1-[2-(methylthio)ethyl]-2(1H)-pyrazinone and 5,7-dichloroindoline as the starting materials. mp 127–128° C.; 1H NMR (300 MHz, CDCl3): 7.19 (d, J=1.8 Hz, 1 H), 7.12 (d, J=2.2 Hz, 1 H), 6.93 (s, 1 H), 4.36 (t, J=8.1 Hz, 2 H), 4.06 (t, J=7.0 Hz, 2 H), 3.13 (t, J=7.9 Hz, 2 H), 2.89 (t, J=7.0 Hz, 2 H), 2.16 (s, 3 H); HRMS (CI) calcd for C15H14N3OSCl3 (M+): 388.9923; found m/z 388.9920.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-31fc14e0e0104080a2ecc91753c187a0
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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