3,5-dichloro-1-methylpropyl-2(1H)-pyrazinone → 3-(7-Bromo-5-methoxy-2,3-dihydro-1H-indol-1-yl)-5-chloro-1-(1-methylpropyl)-2(1H)-pyrazinone

HRID 1271143Notes

Reaction equation

HRID 1271143 reaction equation
[CH:1]([N:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7](Cl)[C:6]1=[O:13])([CH2:3][CH3:4])[CH3:2].Cl.[Br:15][C:16]1[CH:17]=[C:18]([O:25][CH3:26])[CH:19]=[C:20]2[C:24]=1[NH:23][CH2:22][CH2:21]2>>[Br:15][C:16]1[CH:17]=[C:18]([O:25][CH3:26])[CH:19]=[C:20]2[C:24]=1[N:23]([C:7]1[C:6](=[O:13])[N:5]([CH:1]([CH3:2])[CH2:3][CH3:4])[CH:10]=[C:9]([Cl:11])[N:8]=1)[CH2:22][CH2:21]2

Participants

3

Reactant 2

HCID 184527883,5-dichloro-1-methylpropyl-2(1H)-pyrazinoneHCID 184528177-Bromo-5-methoxyindoline hydrochloride

Product 1

HCID 102017743-(7-Bromo-5-methoxy-2,3-dihydro-1H-indol-1-yl)-5-chloro-1-(1-methylpropyl)-2(1H)-pyrazinone

Procedure

Prepared in a similar fashion as described for Example 413 using 1-sec-butyl-3,5-dichloro-2(1H)-pyrazinone and 7-bromo-5-methoxyindoline hydrochloride as the starting materials. mp 155–157° C.; 1H NMR (300 MHz, CDCl3): δ 6.90 (d, J=2.6 Hz, 1 H), 6.78 (s, 1 H), 6.76 (d, J=2.1 Hz, 1 H), 4.99–4.87 (m, 1 H), 4.34 (t, J=7.7 Hz, 2 H), 3.76 (s, 3 H), 3.08 (t, J=7.7 Hz, 2 H), 1.74–1.65 (m, 2 H), 1.34 (d, J=7.0 Hz, 3 H), 0.89 (t, J=7.5 Hz, 3 H); HRMS (ESI) calcd for C20H22N3O2BrCl (M+H)+: 412.0427; found m/z 412.0448.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-7483829b021f4e34bdf53df1a825feea
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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