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

HRID 2251044Notes

Reaction equation

HRID 2251044 reaction equation
Cl[C:2]1[C:3](=[O:13])[N:4]([CH:9]([CH3:12])[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=1.[Br: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>>[Br:14][C:15]1[CH:16]=[C:17]2[C:21](=[C:22]([Cl:24])[CH:23]=1)[N:20]([C:2]1[C:3](=[O:13])[N:4]([CH:9]([CH3:12])[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=1)[CH2:19][CH2:18]2

Participants

3

Reactant 2

HCID 167891645-Bromo-7-chloroindolineHCID 184527883,5-dichloro-1-methylpropyl-2(1H)-pyrazinone

Product 1

HCID 102236823-(5-Bromo-7-chloro-2,3-dihydro-1H-indol-1-yl)-5-chloro-1-methylpropyl-2(1H)-pyrazinone

Procedure

Prepared in a similar fashion as described for Example 413 using 3,5-dichloro-1-methylpropyl-2(1H)-pyrazinone and 5-bromo-7-chloroindoline as the starting materials. mp 150° C.; 1H NMR (300 MHz, CDCl3): δ 7.32 (d, J=1.8 Hz, 1 H), 7.26 (d, J=1.9 Hz, 1 H), 6.85 (s, 1 H), 4.97-4.90 (m, 1 H), 4.34 (t, J=8.1 Hz, 2 H), 3.13 (t, J=7.9 Hz, 2 H), 1.77-1.70 (m, 2 H), 1.36 (d, J=7.0 Hz, 3 H), 0.91 (t, J=7.3 Hz, 3 H); HRMS (ESI) calcd for C16H17N3OBrCl2 (M+H)+: 415.9932; Found m/z 415.9943.

Workup

  1. customPrepared in a similar fashion

Sources & evidence

ORD record
ord-75a0b24ee0a04dcb808c5e3f0ece6d2c
Source dataset
uspto-grants-2008_01
Patent number
US07319100B2

Reaction notes

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