5,7-Dichloroindoline → 5-Chloro-3-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-1-(1-ethylpropyl)-2(1H)-pyrazinone

HRID 1271133Notes

Reaction equation

HRID 1271133 reaction equation
Cl[C:2]1[C:3](=[O:14])[N:4]([CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=1.[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[C:23]([Cl:25])[CH:24]=1)[NH:21][CH2:20][CH2:19]2>>[Cl:8][C:6]1[N:7]=[C:2]([N:21]2[C:22]3[C:18](=[CH:17][C:16]([Cl:15])=[CH:24][C:23]=3[Cl:25])[CH2:19][CH2:20]2)[C:3](=[O:14])[N:4]([CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH:5]=1

Participants

3

Reactant 2

HCID 124822955,7-DichloroindolineHCID 220043393,5-dichloro-1-(1-ethylpropyl)-2(1H)-pyrazinone

Product 1

HCID 101107235-Chloro-3-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-1-(1-ethylpropyl)-2(1H)-pyrazinone

Procedure

Prepared in a similar fashion as described for Example 413 using 3,5-dichloro-1-(1-ethylpropyl)-2(1H)-pyrazinone and 5,7-dichloroindoline as the starting materials. mp 168–170° C.; 1H NMR (300 MHz, CDCl3): δ 7.18 (d, J=1.8 Hz, 1 H), 7.11 (d, J=2.2 Hz, 1 H), 6.78 (s, 1 H), 4.82–4.78 (m, 1 H), 4.35 (t, J=7.9 Hz, 2 H), 3.14 (t, J=8.1 Hz, 2 H), 1.88–1.74 (m, 2 H), 1.70–1.60 (m, 2 H), 0.88 (t, J=7.5 Hz, 6 H); HRMS (ESI) calcd for C17H19N3OCl3 (M+H)+: 386.0594; found m/z 386.0614.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-c49905ced9b6475c8c19d8151cfe41be
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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